5-aryl isoxazolines for controlling invertebrate pests

ABSTRACT

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein A 1 , A 2  and A 3  are independently selected from the group consisting of CR 3  and N; B 1  B 2  and B 3  are independently selected from the group consisting of CR 2  and N; Q is a phenyl ring or a 5- or 6-membered saturated or unsaturated heterocyclic ring, each ring optionally substituted with one or more substituents independently selected from halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, —CN, —NO 2 , —N(R 4 )R 5 , —C(W)N(R4)R 5 , —C(O)OR 5  and R 8 ; or —S(O) 2 N(R 21 )R 22 , —S(O) p R 25  or —S(O)(═NR 28 )R 29 ; and R 1 , R 2 , R 3 , R 4 , R 5 , R 8 , R 21 , R 22 , R 25 , R 28 , R 29 ; p and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition&#39; of the invention.

FIELD OF THE INVENTION

This invention relates to certain isoxazolines, their N-oxides, saltsand compositions suitable for agronomic and nonagronomic uses, includingthose uses listed below, and methods of their use for controllinginvertebrate pests such as arthropods in both agronomic and nonagronomicenvironments.

BACKGROUND OF THE INVENTION

The control of invertebrate pests is extremely important in achievinghigh crop efficiency. Damage by invertebrate pests to growing and storedagronomic crops can cause significant reduction in productivity andthereby result in increased costs to the consumer. The control ofinvertebrate pests in forestry, greenhouse crops, ornamentals, nurserycrops, stored food and fiber products, livestock, household, turf, woodproducts, and public and animal health is also important. Many productsare commercially available for these purposes, but the need continuesfor new compounds that are more effective, less costly, less toxic,environmentally safer or have different modes of action.

PCT Patent Publication WO 05/085216 discloses isoxazoline derivatives ofFormula i as insecticides

wherein, inter alia, each of A¹, A² and A³ are independently C or N; Gis a benzene ring; W is O or S; and X is halogen or C₁-C₆ haloalkyl.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 including allgeometric and stereoisomers, N-oxides, and salts thereof, andcompositions containing them and their use for controlling invertebratepests:

wherein:

-   -   A¹, A² and A³ are independently selected from the group        consisting of CR³ and N;    -   B¹, B² and B³ are independently selected from the group        consisting of CR² and N;    -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more substituents        independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,        C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkyl sulfonyl, C₁-C₆        haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄        alkoxycarbonyl, —CN or —NO₂;    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₂-C₆ alkenyl, C₃-C₆ haloalkenyl, C₂-C₆ alkynyl,        C₃-C₆ haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio,        C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵,        —C(W)OR⁵, —CN or —NO₂;        -   Q is a phenyl ring or a 5- or 6-membered saturated or            unsaturated heterocyclic ring, each ring optionally            substituted with one or more substituents independently            selected from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆            cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆            haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆            alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,            C₁-C₆ haloalkylsulfonyl, —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵,            —C(O)OR⁵ and R⁸; or —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or            —S(O)(═NR²⁸)R²⁹;    -   each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇        cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   each R⁵ is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷;    -   each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂;    -   each R⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN,        —NO₂ or Q¹;    -   each R⁸ is independently a phenyl ring or a pyridinyl ring, each        ring optionally substituted with one or more substituents        independently selected from R⁹;    -   each R⁹ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;    -   each Q¹ is independently a phenyl ring or a 5- or 6-membered        saturated or unsaturated heterocyclic ring, each ring optionally        substituted with one or more substituents independently selected        from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,        C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, —CN, —NO₂, —C(W)N(R¹⁰)R¹¹,        —C(O)OR¹¹ and R¹²;    -   each R¹⁰ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl,        C₄-C₇ cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇        alkoxycarbonyl;    -   each R¹¹ is independently H; or C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇        alkylcycloalkyl, C₄-C₇ cycloalkylalkyl or R¹²;    -   each R¹² is independently a phenyl ring or a pyridinyl ring,        each ring optionally substituted with one or more substituents        independently selected from R¹³;    -   each R¹³ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆            alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇            cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇            alkoxycarbonyl;        -   R²² is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,            C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇            cycloalkylalkyl, each optionally substituted with one or            more substituents independently selected from R²³;    -   each R²³ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂; or a phenyl ring or a pyridinyl ring, each ring        optionally substituted with one or more substituents        independently selected from R²⁴;    -   each R²⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²⁵ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected from R²⁶;    -   each R²⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₂-C₇        alkylcarbonyl, C₂-C₇ alkoxycarbonyl, —CN or —NO₂; or a phenyl        ring or a pyridinyl ring, each ring optionally substituted with        one or more substituents independently selected from R²⁷;    -   each R²⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, alkoxycarbonyl, C₂-C₇        alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²⁸ is H, halogen, —CN, —NO₂, C₂-C₇ alkylcarbonyl, C₂-C₇            haloalkylcarbonyl, C₂-C₇ alkoxycarbonyl, C₂-C₇            alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆            alkylsulfonyl or C₁-C₆ haloalkylsulfonyl; or        -   R²⁸ is C₁-C₆ alkyl, C₃-C₆ cycloalkyl, (C₁-C₆ alkoxy)-(C₁-C₆            alkyl) or C₁-C₆ alkylthio, each optionally substituted with            halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ cycloalkyl,            C₁-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, —CN or            —NO₂;        -   R²⁹ is C₁-C₆ alkyl, C₁₋₇—C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected from R²⁶;    -   each W is independently O or S;        -   p is 0, 1 or 2; and        -   n is 0, 1 or 2.

This invention also provides a composition comprising a compound ofFormula 1, an N-oxide or a salt thereof, and at least one additionalcomponent, selected from the group consisting of a surfactant, a soliddiluent and a liquid diluent. In one embodiment, this invention alsoprovides a composition for controlling an invertebrate pest comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, and at least one additional component selected from thegroup consisting of a surfactant, a solid diluent and a liquid diluent,said composition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent.

This invention further provides a spray composition for controlling aninvertebrate pest comprising a biologically effective amount of acompound of Formula 1, an N-oxide or a salt thereof, or the compositiondescribed above and a propellant. The present invention also providesthe composition described above in the form of a spray compositionwherein the liquid diluent is a propellant. This invention also providesa bait composition for controlling an invertebrate pest comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, or the composition described in the embodiment above,one or more food materials, optionally an attractant, and optionally ahumectant. This invention further provides the composition describedabove in the form of a bait composition wherein the solid diluent and/orthe liquid diluent comprises one or more food materials, saidcomposition optionally comprising an attractant and/or a humectant.

This invention further provides a trap device for controlling aninvertebrate pest comprising said bait composition and a housing adaptedto receive said bait composition, wherein the housing has at least oneopening sized to permit the invertebrate pest to pass through theopening so the invertebrate pest can gain access to said baitcomposition from a location outside the housing, and wherein the housingis further adapted to be placed in or near a locus of potential or knownactivity for the invertebrate pest.

This invention also provides a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of Formula 1, an N-oxideor a salt thereof, (e.g., as a composition described herein). Thisinvention also relates to such method wherein the invertebrate pest orits environment is contacted with a composition comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, and at least one additional component selected from thegroup consisting of a surfactant, a solid diluent and a liquid diluent,said composition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent.

This invention also provides a method for protecting a seed from aninvertebrate pest comprising contacting the seed with a biologicallyeffective amount of a compound of Formula 1, an N-oxide or a saltthereof. This invention further relates to a treated seed comprising acompound of Formula 1, an N-oxide or a salt thereof, in an amount offrom about 0.0001 to 1% by weight of the seed before treatment.

This invention also provides a composition for protecting an animal froman invertebrate parasitic pest comprising a parasitically effectiveamount of a compound of Formula 1, an N-oxide or a salt thereof, and atleast one carrier. The present invention further provides thecomposition described above in a form for oral administration. Thisinvention also provides a method for protecting an animal from aninvertebrate parasitic pest comprising administering to the animal aparasitically effective amount of a compound of Formula 1, an N-oxide ora salt thereof.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains” or “containing,” or any othervariation thereof, are intended to cover a non-exclusive inclusion. Forexample, a composition, a mixture, process, method, article, orapparatus that comprises a list of elements is not necessarily limitedto only those elements but may include other elements not expresslylisted or inherent to such composition, mixture, process, method,article, or apparatus. Further, unless expressly stated to the contrary,“or” refers to an inclusive or and not to an exclusive or. For example,a condition A or B is satisfied by any one of the following: A is true(or present) and B is false (or not present), A is false (or notpresent) and B is true (or present), and both A and B are true (orpresent).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term “invertebrate pest” includesarthropods, gastropods and nematodes of economic importance as pests.The term “arthropod” includes insects, mites, spiders, scorpions,centipedes, millipedes; pill bugs and symphylans. The term “gastropod”includes snails, slugs and other Stylommatophora. The term “helminths”includes worms in the phyla of Nemathelminthes, Platyhelminthes andAcanthocephala such as: round worms, heartworms, and phytophagousnematodes (Nematoda), flukes (Trematoda), tape worms (Cestoda) andthorny-headed worms.

In the context of this disclosure “invertebrate pest control” meansinhibition of invertebrate pest development (including mortality,feeding reduction, and/or mating disruption), and related expressionsare defined analogously.

The term “agronomic” refers to the production of field crops such as forfood and fiber and includes the growth of corn, soybeans and otherlegumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize),leafy vegetables (e.g., lettuce, cabbage, and other cole crops),fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers andcucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g.,pome, stone and citrus), small fruit (berries, cherries) and otherspecialty crops (e.g., canola, sunflower, olives). The term“nonagronomic” refers to settings other than field crops; such as otherhorticultural crops (e.g.; greenhouse, nursery or ornamental plants notgrown in a field), residential, agricultural, commercial and industrialstructures, turf (e.g., sod farm, pasture, golf course, residentiallawn, recreational sports field, etc.), wood products, stored product;agro-forestry and vegetation management, public health (human) andanimal health (e.g., domesticated animals such as pets, livestock andpoultry, undomesticated animals such as wildlife) applications.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkylthio” includes branched or straight-chain alkylthio moieties suchas methylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)—, and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylamino”, “dialkylamino”,and the like, are defined analogously to the above examples.“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups.

The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” include F₃C—, ClCH₂—, CF₃CH₂— andCF₃CCl₂—. The terms “halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, andthe like, are defined analogously to the term “haloalkyl”. Examples of“haloalkoxy” include CF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—.Examples of “haloalkylthio” include CCl₃S—, CF₃S—, CCl₃CH₂S— andClCH₂CH₂CH₂S—. Examples of “haloalkylsulfinyl” include CF₃S(O)—,CCl₃S(O)—, CF₃CH₂S(O)— and CF₃CF₂S(O)—. Examples of “haloalkylsulfonyl”include CF₃S(O)₂—, CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃C(═O)—, CH₃CH₂OC(═O), CH₃CH₂CH₂C(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 7. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., (R²)_(n), n is 1 or 2. When a groupcontains a substituent which can be hydrogen, for example R², then whenthis substituent is taken as hydrogen, it is recognized that this isequivalent to said group being unsubstituted.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and inwhich (4n+2) π electrons, where n is a positive integer, are associatedwith the ring to comply with Hückel's rule.

The terms “heterocyclic ring” or “heterocycle” denote a ring in which atleast one atom forming the ring backbone is not carbon, e.g., nitrogen,oxygen or sulfur. Typically a heterocyclic ring contains no more than 4nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unlessotherwise indicated, a heterocyclic ring can be a saturated, partiallyunsaturated, or fully unsaturated ring. When a fully unsaturatedheterocyclic ring satisfies Hückel's rule, then said ring is also calleda “heteroaromatic ring”, “aromatic heterocyclic ring”. Unless otherwiseindicated, heterocyclic rings and ring systems can be attached throughany available carbon or nitrogen by replacement of a hydrogen on saidcarbon or nitrogen.

The term “optionally substituted” in connection with the heterocyclicrings refers to groups which are unsubstituted or have at least onenon-hydrogen substituent that does not extinguish the biologicalactivity possessed by the unsubstituted analog. As used herein, thefollowing definitions shall apply unless otherwise indicated. The term“optionally substituted” is used interchangeably with the phrase“substituted or unsubstituted” or with the term “(un)substituted.”Unless otherwise indicated, an optionally substituted group may have asubstituent at each substitutable position of the group, and eachsubstitution is independent of the other.

When Q is a 5- or 6-membered nitrogen-containing heterocyclic ring, itmay be attached to the remainder of Formula 1 though any availablecarbon or nitrogen ring atom, unless otherwise described. Similarly,when Q¹ is a 5- or 6-membered nitrogen-containing heterocycle, it may beattached through any available carbon or nitrogen ring atom, unlessotherwise described.

As noted above, Q or Q¹ can be (among others) phenyl optionallysubstituted, with one or more substituents selected from a group ofsubstituents as defined in the Summary of Invention. An example ofphenyl optionally substituted with one to five substituents is the ringillustrated as U-1 in Exhibit 1, wherein R^(v) is selected from a groupof substituents as defined in the Summary of the Invention for Q or Q¹and r is an integer from 0 to 5.

As noted above, Q or Q¹ can be (among others) 5- or 6-memberedheterocyclic ring, which may be saturated or unsaturated, optionallysubstituted: with one or more substituents selected from a group ofsubstituents as defined in the Summary of Invention. Examples of a 5- or6-membered unsaturated aromatic heterocyclic ring optionally substitutedwith from one or more substituents include the rings U-2 through U-61illustrated in Exhibit 1 wherein R^(v) is any substituent as defined inthe Summary of the Invention for Q or Q¹ and r is an integer from 0 to4, limited by the number of available positions on each U group. AsU-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have onlyone available position, for these U groups r is limited to the integers0 or 1, and r being 0 means that the U group is unsubstituted and ahydrogen is present at the position indicated by (R^(v))_(r).

Although R^(v) groups are shown in the structures U-1 through U-61, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H and attached to an atom, this isthe same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

Note that when Q or Q¹ is a 5- or 6-membered saturated or unsaturatednon-aromatic heterocyclic ring optionally substituted with one or moresubstituents selected from the group of substituents as defined in theSummary of Invention for Q or Q¹, one or two carbon ring members of theheterocycle can optionally be in the oxidized form of a carbonyl moiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturatedheterocyclic ring include the rings G-1 through G-35 as illustrated inExhibit 2. Note that when the attachment point on the G group isillustrated as floating, the G group can be attached to the remainder ofFormula 1 through any available carbon or nitrogen of the G group byreplacement of a hydrogen atom. The optional substituents correspondingto R^(v) can be attached to any available carbon or nitrogen byreplacing a hydrogen atom. For these G rings, r is typically an integerfrom 0 to 4, limited by the number available positions on each G group.

Note that when Q or Q¹ comprises a ring selected from G-28 through G-35,G² is selected from O, S or N. Note that when G² is N, the nitrogen atomcan complete its valence by substitution with either H or thesubstituents as defined in the Summary of Invention for Q or Q¹.

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings; forextensive reviews see the eight volume set of Comprehensive HeterocyclicChemistry, A. R. Katritzky and C. W. Rees editors-in-chief, PergamonPress, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers, or as an opticallyactive form.

One skilled in the art will appreciate that not all nitrogen containingheterocyclic rings can form N-oxides since the nitrogen requires anavailable lone pair for oxidation to the oxide; one skilled in the artwill recognize those nitrogen containing heterocyclic rings which canform N-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocyclic rings and tertiary amines are very well knownby one skilled in the art including the oxidation of heterocyclic ringsand tertiary amines with peroxy acids such as per acetic andm-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxidessuch as t-butyl hydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofthe compounds of Formula 1 are useful for control of invertebrate pests(i.e. are agriculturally suitable). The salts of the compounds ofFormula 1 include acid-addition salts with inorganic or organic acidssuch as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include:

Embodiment 1

A compound of Formula 1 wherein R¹ is C₁-C₃ alkyl optionally substitutedwith one or more substituents independently selected from R⁶.

Embodiment 2

A compound of Embodiment 1 wherein R¹ is C₁-C₃ alkyl optionallysubstituted with halogen.

Embodiment 3

A compound of Embodiment 2 wherein R¹ is C₁-C₃ alkyl substituted withhalogen.

Embodiment 4

A compound of Embodiment 3 wherein R¹ is C₁-C₃ alkyl substituted with F.

Embodiment 5

A compound of Embodiment 4 wherein R¹ is C₁-C₃ alkyl fully substitutedwith F.

Embodiment 6

A compound of Embodiment 5 wherein R¹ is CF₃.

Embodiment 7

A compound of Formula 1 wherein each R² is independently H, halogen,C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy or —CN.

Embodiment 8

A compound of Embodiment 7 wherein each R² is independently H, halogen,CF₃, OCF₃ or —CN.

Embodiment 9

A compound of Embodiment 7 wherein each R² is independently H orhalogen.

Embodiment 10

A compound of Formula 1 wherein each R³ is independently H, halogen,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ haloalkenyl, C₂-C₆alkynyl, C₃-C₆ haloalkynyl, C₃-C₆ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —CN or —NO₂.

Embodiment 11

A compound of Embodiment 10 wherein each R³ is independently H, halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄alkynyl, C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CNor —NO₂.

Embodiment 12

A compound of Embodiment 11 wherein each R³ is independently H, halogen,C₁-C₂ alkyl, —C≡CH, —CN or —NO₂.

Embodiment 13

A compound of Embodiment 12 wherein each R³ is H.

Embodiment 14

A compound of Embodiment 12 wherein each R³ is —CN.

Embodiment 15

A compound of Formula 1 wherein Q is a phenyl ring, a pyridinyl ring, apyrimidinyl ring, a triazinyl ring, a pyrazolyl ring, a triazolyl ring,a tetrazolyl ring, an imidazolyl ring, an oxazolyl ring, an isoxazolylthiazolyl ring or an isothiazolyl ring, each ring optionally substitutedwith one or more substituents independently selected from halogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —C(O)OR⁵ and R⁸.

Embodiment 16

A compound of Embodiment 15 wherein Q is a pyrazolyl ring, a triazolylring, a tetrazolyl ring or an imidazolyl ring, each ring attachedthrough nitrogen and optionally substituted with one or moresubstituents independently selected from halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —C(O)OR⁵ and R⁸.

Embodiment 17

A compound of Embodiment 16 wherein Q is a pyrazolyl ring, a triazolylring, a tetrazolyl ring or an imidazolyl ring, each ring attachedthrough nitrogen and optionally substituted with one or moresubstituents independently selected from halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, —CN and —NH₂.

Embodiment 18

A compound of Embodiment 17 wherein Q is a pyrazolyl ring, a triazolylring, a tetrazolyl ring or an imidazolyl ring, each ring attachedthrough nitrogen.

Embodiment 19

A compound of Formula 1 wherein each R⁴ is independently H, C₁-C₄ alkyl,C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl.

Embodiment 20

A compound of Embodiment 19 wherein each R⁴ is H.

Embodiment 21

A compound of Formula 1 wherein each R⁵ is independently H; or C₁-C₄alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C₇alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each optionally substitutedwith one or more substituents independently selected from R⁷.

Embodiment 22

A compound of Embodiment 21 wherein each R⁵ is independently H; or C₁-C₄alkyl optionally substituted with one or more substituents independentlyselected from R⁷.

Embodiment 23

A compound of Embodiment 22 wherein each R⁵ is independently H or C₁-C₄alkyl.

Embodiment 24

A compound of Formula 1 wherein each R⁷ is independently halogen, C₁-C₄alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, —CN, —NO₂ or Q¹.

Embodiment 25

A compound of Formula 1 wherein Q¹ is a phenyl ring, a pyridinyl ring, atriazolyl ring, a pyrazolyl ring, a triazolyl ring or an imidazolylring, each ring optionally substituted with one or more substituentsindependently selected from halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, —CN,—C(N)N(R¹⁰)R¹¹, C(O)OR¹¹ and R¹².

Embodiment 26

A compound of Formula 1 wherein each R¹⁰ is independently H, C₁-C₄alkyl, C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl.

Embodiment 27

A compound of Embodiment 26 wherein each R¹⁰ is H.

Embodiment 28

A compound of Formula 1 wherein each R¹¹ is independently H; or C₁-C₄alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C₇alkylcycloalkyl, C₄-C₇ cycloalkylalkyl or R¹².

Embodiment 29

A compound of Embodiment 28 wherein each R¹¹ is H or C₁-C₄ alkyl.

Embodiment 30

A compound of Formula 1 wherein Q is —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or—S(O)(═NR²⁸)R²⁹.

Embodiment 31

A compound of Formula 1 wherein Q is —S(O)₂N(R²¹)R²².

Embodiment 32

A compound of Formula 1 wherein R²¹ is H or C₁-C₆ alkyl.

Embodiment 33

A compound of Embodiment 32 wherein R²¹ is H or methyl.

Embodiment 34

A compound of Formula 1 wherein R²² is H; or C₁-C₄ alkyl, C₂-C₄ alkenyl,C₂-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²³.

Embodiment 35

A compound of Embodiment 34 wherein R²² is C₁-C₄ alkyl optionallysubstituted with one or more substituents independently selected fromR²³.

Embodiment 36

A compound of Formula 1 wherein each R²³ is independently halogen, C₁-C₄alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, —CN or —NO₂; or a phenyl ring or a pyridinyl ring, eachring optionally substituted with one or more substituents independentlyselected from R²⁴.

Embodiment 37

A compound of Embodiment 36 wherein each R²³ is independently halogen,C₁-C₄ alkylthio, —CN, a phenyl ring or a pyridinyl ring.

Embodiment 38

A compound of Formula 1 wherein Q is —S(O)_(p)R²⁵.

Embodiment 39

A compound of Formula 1 wherein R²⁵ is C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²⁶.

Embodiment 40

A compound of Embodiment 39 wherein R²⁵ is C₁-C₄ alkyl optionallysubstituted with one or more substituents independently selected fromR²⁶.

Embodiment 41

A compound of Embodiment 40 wherein R²⁵ is methyl, ethyl or CH₂CF₃.

Embodiment 42

A compound of Formula 1 wherein each R²⁶ is independently halogen, C₁-C₄alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CNor —NO₂.

Embodiment 43

A compound of Embodiment 42 wherein each R²⁶ is independently halogen or—CN.

Embodiment 44

A compound of Formula 1 wherein Q is —S(O)(═NR²⁸)R²⁹.

Embodiment 45

A compound of Formula 1 wherein R²⁸ is H, halogen, C₁-C₄ alkyl, —CN,—NO₂, C₂-C₇ haloalkylcarbonyl or C₂-C₇ alkoxycarbonyl.

Embodiment 46

A compound of Embodiment 45 wherein R²⁸ is H, C₁-C₄ alkyl, —CN or —NO₂.

Embodiment 47

A compound of Formula 1 wherein R²⁹ is C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²⁶.

Embodiment 48

A compound of Embodiment 47 wherein R²⁹ is C₁-C₄ alkyl optionallysubstituted with one or more substituents independently selected fromR²⁶.

Embodiment 49

A compound of Embodiment 48 wherein R²⁹ is methyl, ethyl or CH₂CF₃.

Embodiment 50

A compound of Formula 1 wherein W is O.

Embodiment 51

A compound of Formula 1 wherein n is 0.

Embodiment 52

A compound of Formula 1 Wherein p is 1 or 2.

Embodiment 53

A compound of Formula 1 wherein A¹ and A² are CR³; and A³ is CR³ or N.

Embodiment 54

A compound of Embodiment 53, wherein A³ is CR³.

Embodiment 55

A compound of Formula 1 wherein A¹ is N; and A² and A³ are CR³.

Embodiment 56

A compound of Formula 1 wherein A² is N; and A¹ and A³ are CR³.

Embodiment 57

A compound of Formula 1 wherein A¹ is CR³; and A² and A³ are N.

Embodiment 58

A compound of Formula 1 wherein A² is CR³; and A¹ and A³ are N.

Embodiment 59

A compound of Formula 1 wherein A³ is CR³; and A¹ and A² are N.

Embodiment 60

A compound of Formula 1 wherein B¹, B² and B³ are CR².

Embodiment 61

A compound of Embodiment 60 wherein B² is CH.

Embodiment 62

A compound of Formula 1 wherein B¹ is N; and B² and B³ are CR².

Embodiment 63

A compound of Formula 1 wherein B² is N; and B¹ and B³ are CR².

Embodiment 64

A compound of Formula 1 wherein B² is CR²; and B¹ and B³ are N.

Embodiment 65

A compound of Formula 1 wherein R²⁸ is other than halogen.

Embodiments of this invention, including Embodiments 1-65 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds. In addition, embodiments of this invention,including Embodiments 1-65 above as well as any other embodimentsdescribed herein, and any combination thereof, pertain to thecompositions and methods of the present invention.

Combinations of Embodiments 1-65 can be illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   A¹ and A² are CR³;    -   A³ is CR³ or N;    -   B¹, B² and B³ are CR²;    -   R¹ is C₁-C₃ alkyl optionally substituted with one or more        substituents independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ haloalkyl, C₁-C₆        haloalkoxy or —CN;    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₂-C₆ alkenyl, C₃-C₆ haloalkenyl, C₂-C₆ alkynyl,        C₃-C₆ haloalkynyl, C₃-C₆ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —CN or —NO₂;    -   each R⁴ is independently H, C₁-C₄ alkyl, C₂-C₄ alkylcarbonyl or        C₂-C₄ alkoxycarbonyl;    -   each R⁵ is independently H; or C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄        alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷;    -   each R⁷ is independently halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy,        C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CN,        —NO₂ or Q¹;        -   Q¹ is a phenyl ring, a pyridinyl ring, a thiazolyl ring, a            pyrazolyl ring, a triazolyl ring or an imidazolyl ring, each            ring optionally substituted with one or more substituents            independently selected from halogen, C₁-C₃ alkyl, C₁-C₃            haloalkyl, —CN, —C(W)N(R¹⁰)R¹¹, C(O)OR¹¹ and R¹²;    -   each R¹⁰ is independently H, C₁-C₄ alkyl, C₂-C₄ alkylcarbonyl or        C₂-C₄ alkoxycarbonyl; and    -   each R¹¹ is independently H; or C₁-C₄ alkyl, C₃-C₄ alkenyl,        C₃-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇        cycloalkylalkyl or R¹².

Embodiment B

A compound of Embodiment A wherein

-   -   Q is a phenyl ring, a pyridinyl ring, a pyrimidinyl ring, a        triazinyl ring, a pyrazolyl ring, a triazolyl ring, a tetrazolyl        ring, an imidazolyl ring, an oxazolyl ring, an isoxazolyl ring,        a thiazolyl ring or an isothiazolyl ring, each ring optionally        substituted with one or more substituents independently selected        from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,        C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —C(O)OR⁵ and R⁸.

Embodiment C

A compound of Embodiment B wherein

-   -   R¹ is C₁-C₃ alkyl optionally substituted with halogen;    -   each R² is independently H, halogen, CF₃, OCF₃ or —CN;    -   each R³ is independently H, halogen, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl,        C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN        or —NO₂;    -   each R⁴ is H;        -   Q is a pyrazolyl ring, a triazolyl ring, a tetrazolyl ring            or an imidazolyl ring, each ring attached through nitrogen            and optionally substituted with one or more substituents            independently selected from halogen, C₁-C₄ alkyl, C₁-C₄            haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₄            alkoxy, C₁-C₄ haloalkoxy, —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵,            —C(O)OR⁵ and R⁸; and        -   W is O.

Embodiment D

A compound of Embodiment C wherein

-   -   A³ is CR³;    -   B² is CH;    -   R¹ is CF₃;    -   each R² is independently H or halogen;    -   each R³ is independently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or        —NO₂; and        -   Q is a pyrazolyl ring, a triazolyl ring, a tetrazolyl ring            or an imidazolyl ring, each ring attached through nitrogen            and optionally substituted with one or more substituents            independently selected from halogen, C₁-C₄ alkyl, C₁-C₄            haloalkyl, —CN and —NH₂.

Embodiment E

A compound of Embodiment A wherein

-   -   Q is —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or —S(O)(═NR²⁸)R²⁹;    -   R²¹ is H or C₁-C₆ alkyl;    -   R²² is C₁-C₄ alkyl optionally substituted with one or more        substituents independently selected from R²³;    -   each R²³ is independently halogen, C₁-C₄ alkylthio, —CN, a        phenyl ring or a pyridinyl ring;        -   R²⁵ is C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, —C₃-C₄            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected from R²⁶;    -   each R²⁶ is independently halogen, C₁-C₄ alkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CN or        —NO₂;        -   R²⁸ is H, halogen, C₁-C₄ alkyl, —CN, —NO₂, C₂-C₇            haloalkylcarbonyl or C₂-C₇ alkoxycarbonyl; and        -   R²⁹ is C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected, from R²⁶.

Embodiment F

A compound of Embodiment E wherein

-   -   R¹ is C₁-C₃ alkyl optionally substituted with halogen;    -   each R² is independently H, CF₃, OCF₃, halogen or —CN;    -   each R³ is independently H, halogen, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl,        C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN        or —NO₂;    -   each R⁴ is H;        -   Q is —S(O)₂N(R²¹)R²²;        -   R²¹ is H or methyl; and        -   W is O.

Embodiment G

A compound of Embodiment F wherein

-   -   A³ is CR³;    -   B² is CH;    -   R¹ is CF₃;    -   each R² is independently H or halogen; and    -   each R³ is independently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or        —NO₂.

Embodiment H

A compound of Embodiment E wherein

-   -   R¹ is C₁-C₃ alkyl optionally substituted with halogen;    -   each R² is independently H, CF₃, OCF₃, halogen or —CN;    -   each R³ is independently H, halogen, C₁-C₄ alkyl; C₁-C₄        haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl,        C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN        or —NO₂;    -   each R⁴ is H;        -   Q is —S(O)_(p)R²⁵;        -   R²⁵ is C₁-C₄ alkyl optionally substituted with one or more            substituents independently selected from R²⁶;    -   each R²⁶ is independently halogen or —CN;        -   W is O; and        -   p is 1 or 2.

Embodiment I

A compound of Embodiment H wherein

-   -   A³ is CR³;    -   B² is CH;    -   R¹ is CF₃;    -   each R² is independently H or halogen; and    -   each R³ is independently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or        —NO₂.

Embodiment J

A compound of Embodiment E wherein

R¹ is C₁-C₃ alkyl optionally substituted with halogen;

-   -   each R² is independently H, CF₃, OCF₃, halogen or —CN;    -   each R³ is independently H, halogen, C₁-C₄ alkyl, C₁-C₄        haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl,        C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN        or —NO₂;    -   each R⁴ is H;        -   Q is —S(O)(═NR²⁸)R²⁹;        -   R²⁸ is H, C₁-C₄ alkyl, —CN or —NO₂;        -   R²⁹ is C₁-C₄ alkyl optionally substituted with one or more            substituents independently selected from R²⁶;    -   each R²⁶ is independently halogen or —CN; and        -   W is O.

Embodiment K

A compound of Embodiment J wherein

-   -   A³ is CR³;    -   B² is CH;    -   R¹ is CF₃;    -   each R² is independently H or halogen; and    -   each R³ is independently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or        —NO₂.

Specific embodiments include compounds of Formula 1 selected from thegroup consisting of:

-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)-isoxazole;-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;-   2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]-pyridine;-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;-   1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]-1H-1,2,4-triazole;-   1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-phenyl]-1H-1,2,4-triazole;-   1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-phenyl]-1H-1,2,3-triazole;-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile;-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,3-triazol-1-yl)benzenecarbothioamide;-   2-(3-amino-1H-1,2,4-triazol-1-yl)-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)₌3-isoxazolyl]benzonitrile;-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-tetrazol-1-yl)benzonitrile;-   N-(cyclopropylmethyl)-4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzenesulfonamide;-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(2-pyridinylmethyl)benzenesulfonamide;-   5-[5-(3,5-dibromophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile;-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)isoxazole;-   5-[(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylsulfonyl)benzonitrile;    and-   3-[3-bromo-4-(methylthio)phenyl]-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole.

Further specific embodiments include any combination of the compounds ofFormula 1 selected from the group immediately above.

Embodiments of the present invention further include:

Embodiment A1

A compound of Formula 1q, an N-oxide, or a salt thereof,

wherein:

-   -   A is selected from the group consisting of CR³ and N;    -   B¹, B² and B³ are independently selected from the group        consisting of CR² and N;    -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more substituents        independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,        C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN        or —NO₂;    -   each R³ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ alkenyl, C₃-C₆ haloalkenyl, C₂-C₆ alkynyl; C₃-C₆        haloalkynyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio,        C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵,        —C(W)OR⁵, —CN or —NO₂;        -   Q is a phenyl ring or a 5- or 6-membered saturated or            unsaturated heterocyclic ring, each ring optionally            substituted with one or more substituents independently            selected from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆            cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆            haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆            alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,            C₁-C₆ haloalkylsulfonyl, —CN, —NO₂, —N(R⁴)R⁵, —C(W)N(R⁴)R⁵,            —C(O)OR⁵ and R⁸; or —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or            —S(O)(═NR²⁸)R²⁹;    -   each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇        cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   each R⁵ is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷;    -   each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂;    -   each R⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN,        —NO₂ or Q¹;    -   each R⁸ is independently a phenyl ring or a pyridinyl ring, each        ring optionally substituted with one or more substituents        independently selected from R⁹;    -   each R⁹ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₇-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkyl aminocarbonyl, —OH,        —NH₂, —COOH, —CN or —NO₂;    -   each Q¹ is independently a phenyl ring or a 5- or 6-membered        saturated or unsaturated heterocyclic ring, each ring optionally        substituted with one or more substituents independently selected        from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl;        C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, —CN, —NO₂, —C(W)N(R¹⁰)R¹¹,        —C(O)OR¹¹ and R¹²;    -   each R¹⁰ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl,        C₄-C₇ cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇        alkoxycarbonyl;    -   each R¹¹ is independently H; or C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇        alkylcycloalkyl, C₄-C₇ cycloalkylalkyl or R¹²;    -   each R¹² is independently a phenyl ring or a pyridinyl ring,        each ring optionally substituted with one or more substituents        independently selected from R¹³;    -   each R¹³ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆            alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl,            cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇            alkoxycarbonyl;        -   R²² is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,            C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇            cycloalkylalkyl, each optionally substituted with one or            more substituents independently selected from R²³;    -   each R²³ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂; or a phenyl ring or a pyridinyl ring, each ring        optionally substituted with one or more substituents        independently selected from R²⁴;    -   each R²⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²⁵ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected from R²⁶;    -   each R²⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₂-C₇        alkyl carbonyl, C₂-C₇ alkoxycarbonyl, —CN or —NO₂; or a phenyl        ring or a pyridinyl ring, each ring optionally substituted with        one or more substituents independently selected from R²⁷;    -   each R²⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino,        C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂,        —COOH, —CN or —NO₂;        -   R²⁸ is H, —CN, —NO₂, C₂-C₇ alkylcarbonyl, C₂-C₇            haloalkylcarbonyl, C₂-C₇ alkoxycarbonyl, C₂-C₇            alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, C₁-C₆            alkylsulfonyl or C₁-C₆ haloalkylsulfonyl; or        -   R²⁸ is C₁-C₆ alkyl, C₃-C₆ cycloalkyl, (C₁-C₆ alkoxy)-(C₁-C₆            alkyl) or C₁-C₆ alkylthio, each optionally substituted with            halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ cycloalkyl,            C₁-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy; —CN or            —NO₂;        -   R²⁹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆            cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl,            each optionally substituted with one or more substituents            independently selected from R²⁶;    -   each W is independently O or S;        -   p is 0, 1 or 2;        -   m is 1, 2 or 3; and        -   n is 1 or 2.

Embodiment AA

A compound of Formula 1p, an N-oxide, or a salt thereof,

wherein:

-   -   A is selected from the group consisting of CR³ and N;    -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more substituents        independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,        C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN        or —NO₂;    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkyl sulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        —CN or —NO₂;        -   Q is a phenyl ring or a 5- or 6-membered saturated or            unsaturated heterocyclic ring, each ring optionally            substituted with one or more substituents independently            selected from the group halogen, C₁-C₆ alkyl, C₁-C₆            haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆            alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆            haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,            C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆            alkylamino, C₂-C₆ dialkylamino, —CN, —NO₂, C(W)N(R⁴)R⁵,            C(O)OR⁵ and R⁸;    -   each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇        cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   each R⁵ is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷;    -   each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂;    -   each R⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂; or Q¹;    -   each R⁸ is independently a phenyl ring or a pyridinyl ring, each        ring optionally substituted with one or more substituents        independently selected from R⁹;    -   each R⁹ is independently halogen, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, dialkylamino, C₂-C₄        alkoxycarbonyl, —CN or —NO₂;    -   each Q¹ is independently a phenyl ring or a 5- or 6-membered        saturated or unsaturated heterocyclic ring, each ring optionally        substituted with one or more substituents independently selected        from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,        C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, CN, NO₂, C(W)N(R¹⁰)R¹¹,        C(O)OR¹¹ or R¹²;    -   each R¹⁰ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl,        C₄-C₇ cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇        alkoxycarbonyl;    -   each R¹¹ is independently H; or C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇        alkylcycloalkyl, C₄-C₇ cycloalkylalkyl or R¹²;    -   each R¹² is independently a phenyl ring or a pyridinyl ring,        each ring optionally substituted with one or more substituents        independently selected from R⁹;    -   each W is independently O or S;        -   m is 1, 2 or 3; and        -   n″ is 1, 2, 3, 4 or 5.

Embodiment BB

A compound of Embodiment AA wherein

-   -   Q is a phenyl ring or a 5- or 6-membered saturated or        unsaturated heterocyclic ring, each ring optionally substituted        with one or more substituents independently selected from the        group halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,        C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, CN, NO₂, C(W)N(R⁴)R⁵,        C(O)OR⁵ and R⁸; provided that when Q is a 5-membered        nitrogen-containing heterocyclic ring Q is attached through        nitrogen.

Embodiment CC

A compound of Embodiment BB wherein

-   -   R¹ is C₁-C₃ alkyl optionally substituted with one or more        substituents selected from R⁶;    -   each R² is independently selected from the group consisting of        H, halogen, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy and CN;    -   each R³ is independently selected from the group consisting of        H, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, CN and NO₂;        -   Q is a phenyl ring, a pyridinyl ring, a pyrimidinyl ring, a            triazinyl ring, a pyrazolyl ring, a triazolyl ring, an            imidazolyl ring, an oxazolyl ring, an isoxazolyl ring, a            thiazolyl ring or an isothiazolyl ring, each ring optionally            substituted with one or more substituents independently            selected from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆            cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆            haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆            alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,            C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆            dialkylamino, CN, NO₂, C(W)N(R⁴)R⁵, C(O)OR⁵ and R⁸;    -   each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₇ alkylcarbonyl or        C₂-C₇ alkoxycarbonyl;    -   each R⁵ is independently or C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄        alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents selected from R⁷;    -   each R⁷ is independently selected from group consisting of        halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CN and —NO₂; or Q¹; and        -   Q¹ is a phenyl ring, a pyridinyl ring, a thiazolyl ring, a            pyrazolyl ring, a triazolyl ring or an imidazolyl ring, each            ring optionally substituted with one or more substituents            independently selected from halogen, C₁-C₃ alkyl, C₁-C₃            haloalkyl, CN, C(O)N(R¹⁰)R¹¹, C(O)OR¹¹ and R¹².

Embodiment DD

A compound of Embodiment CC wherein

R¹ is C₁-C₃ alkyl optionally substituted with halogen;

-   -   each R² is independently selected from the group consisting of        H, CF₃, OCF₃, halogen and CN;    -   each R³ is independently selected from group consisting of H,        halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₁-C₄        alkoxy, CN and NO₂;        -   Q is a pyrazolyl ring, a triazolyl ring or an imidazolyl            ring, each ring attached through nitrogen and optionally            substituted with one or more substituents independently            selected from halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆            cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₄ alkoxy, C₁-C₄            haloalkoxy, C₁-C₄ alkylamino, C₂-C₄ dialkylamino, CN, NO₂,            C(W)N(R⁴)R⁵, C(O)OR⁵ and R⁸;        -   R⁴ is H; and        -   W is O.

Embodiment EE

A compound of Embodiment DD wherein

-   -   R¹ is CF₃; and    -   n″ is 1 or 2.

Specific embodiments include compounds of Formula 1p selected from thegroup consisting of:

-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;-   2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]pyridine;-   5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;    and-   1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]-1H-1,2,4-triazole.

Of note is that compounds of this invention are characterized byfavorable metabolic and/or soil residual patterns and exhibit activitycontrolling a spectrum of agronomic and nonagronomic invertebrate pests.

Of particular note, for reasons of invertebrate pest control spectrumand economic importance, protection of agronomic crops from damage orinjury caused by invertebrate pests by controlling invertebrate pestsare embodiments of the invention. Compounds of this invention because oftheir favorable translocation properties or systemicity in plants alsoprotect foliar or other plant parts which are not directly contactedwith a compound of Formula 1 or a composition comprising the compound.

Also noteworthy as embodiments of the present invention are compositionscomprising a compound of any of the preceding Embodiments, as well asany other embodiments described herein, and any combinations thereof,and at least one additional component selected from the group consistingof a surfactant, a solid diluent and a liquid diluent, said compositionsoptionally, further comprising at least one additional biologicallyactive compound or agent.

Further noteworthy as embodiments of the present invention arecompositions for controlling an invertebrate pest comprising abiologically effective amount of a compound of any of the precedingEmbodiments, as well as any other embodiments described herein, and anycombinations thereof, and at least one additional component selectedfrom the group consisting of a surfactant, a solid diluent and a liquiddiluent, said composition optionally further comprising a biologicallyeffective amount of at least one additional biologically active compoundor agent. Embodiments of the invention further include methods forcontrolling an invertebrate pest comprising contacting the invertebratepest or its environment with a biologically effective amount of acompound of any of the preceding Embodiments (e.g., as a compositiondescribed herein).

Embodiments of the invention also include a composition comprising acompound of any of the preceding Embodiments, in the form of a soildrench liquid formulation. Embodiments of the invention further includemethods for controlling an invertebrate pest comprising contacting thesoil with a liquid composition as a soil drench comprising abiologically effective amount of a compound of any of the precedingEmbodiments.

Embodiments of the invention also include a spray composition forcontrolling an invertebrate pest comprising a biologically effectiveamount of a compound of any of the preceding Embodiments and apropellant. Embodiments of the invention further include a baitcomposition for controlling an invertebrate pest comprising abiologically effective amount of a compound of any of the precedingEmbodiments, one or more food materials, optionally an attractant, andoptionally a humectant. Embodiments of the invention also include adevice for controlling an invertebrate pest comprising said baitcomposition and a housing adapted to receive said bait composition,wherein the housing has at least one opening sized to permit theinvertebrate pest to pass through the opening so the invertebrate pestcan gain access to said bait composition from a location outside thehousing, and wherein the housing is further adapted to be placed in ornear a locus of potential or known activity for the invertebrate pest.

Embodiments of the invention also include a method for protecting a seedfrom an invertebrate pest comprising contacting the seed with abiologically effective amount of a compound any of the precedingEmbodiments. Embodiments of the invention further include a treated seedcomprising a compound of any of the preceding Embodiments in an amountof from about 0.0001 to 1% by weight of the seed before treatment.

Embodiments of the invention also include a composition for protectingan animal from an invertebrate parasitic pest comprising aparasiticidally effective amount of a compound of any of the precedingEmbodiments and at least one carrier. Embodiments of the invention alsoinclude a composition comprising a compound of any of the precedingEmbodiments in a form for oral administration. Embodiments of theinvention further include a method for protecting an animal from aninvertebrate parasitic pest comprising administering to the animal aparasiticidally effective amount of a compound of any of the precedingEmbodiments.

Compounds of Formula 1 can be prepared by one or more of the followingmethods and variations as described in Schemes 1-8. The definitions ofR¹, R², R³, R²⁵, A¹, A², A³, B¹, B², B³, n, p and Q in the compounds ofFormulae 1-10 below are as defined above for Formula 1 in the Summary ofthe Invention. Compounds of Formulae 1a and 1b are subsets of compoundsof Formula 1. Compounds of Formula 2a are a subset of compounds ofFormula 2.

Compounds of Formula 1 can be prepared by the cycloaddition of compoundsof Formula 2 with nitrile oxides derived from oximes of Formula 3 asoutlined in Scheme 1. The reaction typically proceeds through theintermediacy of an in situ generated hydroxamyl chloride. In a typicalprocedure a chlorinating reagent such as sodium hypochlorite,N-chlorosuccinimide, or chloramine-T is combined with the oxime in thepresence of the styrene. Depending on the conditions amine bases such aspyridine or triethylamine may be necessary. The reaction can be run in awide variety of solvents including tetrahydrofuran, diethyl ether,methylene chloride, dioxane, and toluene with optimum temperaturesranging from room temperature to the reflux temperature of the solvent.Example 1, Step B illustrates a typical procedure for this reaction.General procedures for cycloaddition of nitride oxides with olefins arewell documented in the chemical literature. For relevant references seeLee, Synthesis, 1982, 6, 508-509 and Kanemasa et al., Tetrahedron, 2000,56, 1057-1064 as well as references cited within.

Compounds of Formula 1, wherein Q is a 5-membered N-linked heterocyclicring can also be prepared by direct displacement of an aromatic halideof Formula 4 wherein Y is Br or F with an azole heterocyclic ring ofFormula 5 as shown in Scheme 2. Typical azole heterocyclic rings ofFormula 5 include optionally substituted pyrazoles, imidazoles,triazoles and tetrazoles. Bromides can be displaced with the use ofcopper iodide and a palladium catalyst, see for example Kanemasa et al.,European Journal of Organic Chemistry, 2004, 695-709. For directfluorine displacement the reaction is typically run in a polar aproticsolvent such as N,N-dimethylformamide or N,N-dimethylacetamide and inthe presence of an inorganic base such as sodium or potassium carbonate.Example 2, Step C illustrates a typical procedure for this type ofreaction.

An alternate preparation for the compounds of Formula 1 wherein Q is aphenyl or aromatic heterocyclic ring includes the well known Suzukireaction via Pd-catalyzed cross coupling of an aromatic iodide orbromide of Formula 4 wherein Y is Br or I with an aryl or heteroarylboronic acid of Formula 6 (Scheme 3). Many catalysts are useful for thistype of transformation; a typical catalyst istetrakis(triphenylphosphine)palladium(0). Solvents such astetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable.The boronic acids of Formula 6 are either commercially available or canbe prepared by known methods. Other methods including the Heck, Stille,Kumada and Buchwald-Hartwig coupling procedures offer many alternativesfor introduction of Q heterocyclic groups. For leading references seefor example Zificsak, Craig A and Hlasta, Dennis J., Tetrahedron, 2004,60, 8991-9016. For a thorough review of palladium chemistry applicableto the synthesis of heterocyclic Q groups see Li, J. J.; Gribble, G. W.;Editors. Palladium in Heterocyclic Chemistry: A Guide for the SyntheticChemist, Elsevier: Oxford, UK, 2000.

The oximes of Formula 3 are available by contacting the correspondingaldehydes of Formula 7 with hydroxylamine according to known methods asshown in Scheme 4. The aldehydes can be prepared by known syntheticprocedures, and many are known compounds, some being commerciallyavailable.

A wide variety of alternate methods exist for the preparation ofheterocyclic Q groups found in Formula 1. These can be prepared fromwell documented functional group transformations of ketones, esters,acids, aldehydes, nitriles and the like. For leading references seeTanaka et al., J. Med Chem, 1998, 41, 2390-2410 and references citedwithin.

An especially useful group of styrenes for the synthesis of compounds ofFormula 1 are represented by Formula 2a as shown in Scheme 5. Theseintermediates can be prepared by the palladium-catalyzed coupling ofcommercially available 2-bromo-3,3,3-trifluoropropene (Formula 8) witharyl boronic acids of Formula 9. General procedures for this reactionare documented in the chemical literature, see Pan et al., J. FluorineChemistry, 1999, 95, 167-170. A typical procedure using modifiedconditions is described in Example 1, Step A.

Compounds of Formula 1, wherein Q is S(O)₂NR²¹R²² can be prepared inthree steps by direct displacement of an aromatic halide of Formula 4wherein Y is Cl, Br or F with a mercaptan such as benzylmercaptan,followed by oxidation to the sulfonyl chloride and subsequent conversionto the sulfonamide by reaction with an amine (Scheme 6). Typicaldisplacement reactions involve treatment of the aromatic halide ofFormula 4 with the mercaptan in a polar aprotic solvent such as such asN,N-dimethylformamide or N,N-dimethylacetamide and in the presence of aninorganic base such as sodium, potassium or cesium carbonate. Oxidationof the benzylthioether intermediate to the corresponding sulfonylchloride is readily accomplished with 5% sodium hypochlorite (commercialbleach) in solvents such as methylene chloride or chloroform. Conversionto the sulfonamide is accomplished by known literature proceduresinvolving treatment of the sulfonyl chloride with a amine (HNR²¹R²²) inthe presence of an acid scavenger such as pyridine, triethylamine orother amine bases. In certain instances it may be convenient to useexcess amine as both the nucleophile and acid scavenger. Example 4illustrates a typical procedure for preparing compounds of Formula 1wherein Q is S(O)₂NR²¹R²².

Compounds of Formula 1a (i.e. Formula 1 wherein Q is S(O)_(p)R²⁵ and pis 0) can be prepared by direct displacement of an aromatic halide ofFormula 4 wherein Y is Cl, Br or F with a mercaptan or its alkali metalsalt, such as methylmercaptan or sodium thiomethoxide. Oxidation of thethioether group of Formula 1a to the sulfinyl or sulfonyl group (i.e.Formula 1 wherein Q is S(O)R²⁵ and p is 1 or 2) can be accomplished bymethods very familiar to one skilled in the art (Scheme 7). Typicaldisplacement reaction involves treatment of the aromatic halide ofFormula 4 with the mercaptan in a polar aprotic solvent such asN,N-dimethylformamide or N,N-dimethylacetamide and in the presence of aninorganic base such as sodium, potassium or cesium carbonate, or by useof a salt of the mercaptan (as shown in Scheme 7). The mercaptan salt iseither commercially available or can be prepared separately by treatmentof the mercaptan with a strong base such as sodium hydride. Oxidation ofthe thioether compounds of Formula 1a to the sulfinyl or sulfonylcompounds of Formula 1 wherein Q is S(O)_(p)R²⁵ and p is 1 or 2 isreadily accomplished by reaction with sodium metaperiodate or Oxone®(potassium peroxymonosulfate) in solvents such as water or alcohols, or3-chloroperoxybenzoic acid (MCPBA) in solvents such as methylenechloride or chloroform.

Alternatively, compounds of Formula 1a can be prepared by metal-halogenexchange of an aromatic halide of Formula 4 wherein Y is Br or I withn-BuLi, followed by reaction with a sulfur-containing reagent (e.g.,ethyl disulfide or methyl methanethiolsulfonate). Compounds of Formula1a can also be prepared by transition metal-catalyzed reaction of anaromatic halide or trifluoromethanesulfonate of Formula 4 wherein Y isBr, I or OSO₂CF₃ with a mercaptan salt such astriisopropylsilylmercaptan sodium salt, or sodium sulfonate, followed byalkylating with a halide such as I—R²⁵ in the presence of a phasetransfer catalyst such as tetrabutylammonium fluoride. Example 5illustrates typical procedure for preparing compounds of Formula 1wherein Q is S(O)_(p)R²⁵ and p is 0. Examples 6 and 7 illustrate typicalprocedures for preparing compounds of Formula 1 wherein Q is S(O)_(p)R²⁵and p is 2.

Compounds of Formula 1b (i.e. Formula 1 wherein Q is S(O)_(p)R²⁵ and pis 2) can be prepared by treatment of a sulfonyl chloride of Formula 10with reducing reagents as sodium sulfite (Na₂SO₃), followed by treatmentof the resulting sulfonate salt with an alkylating agent and base toafford the sulfone of Formula 1b.

Sulfonyl chlorides of Formula 10 can be prepared by the reactionsillustrated in Scheme 6 involving direct displacement of an aryl halideof Formula 4 with a mercaptan such as benzylmercaptan followed byoxidation to the sulfonyl chloride.

Compounds of Formula 4 can be prepared analogously by the methodsdescribed for compounds of Formula 1 in Scheme 1.

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “t” meanstriplet, “q” means quartet, “AB q” means AB quartet, “m” meansmultiplet, “dd” means doublet of doublets, “dt” means doublet oftriplets, “br s” means broad singlet and “br t” means broad triplet.

Example 1 Preparation of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazoleStep A: Preparation of1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene

To a mixture of tetrahydrofuran (33 mL), ethylene glycol dimethyl ether(33 mL), and 4 N aqueous potassium hydroxide (33 mL) in a 200 mLFisher-Porter sealed tube was added 3,5-dichlorophenylboronic acid (8.72g, 45.7 mmol) and 2-bromo-3,3,3-trifluoro-propene (10.0 g, 57.2 mmol),followed by the addition of tetrakis(triphenylphosphine)-palladium(0)(264 mg, 0.229 mmol). The mixture was heated to 75° C. for 3′ h. Thenthe reaction mixture was partitioned between diethyl ether and water.The aqueous extract was washed with diethyl ether (2×20 mL). The organicextracts were combined, dried (MgSO₄), and concentrated under reducedpressure to provide a residue. The residue was purified by silica gelchromatography and eluted with hexane to afford 4.421 g of the titlecompound as a clear oil.

¹H NMR (CDCl₃) δ 7.41 (s, 2H), 7.33 (s, 1H), 6.04 (d, 1H), 5.82 (d, 1H).

Step B Preparation of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-pyrazol-1-yl)-phenyl]-5-(trifluoromethyl)isoxazole

To a solution of 4-(1H-pyrazol-1-yl)benzaldehyde (1.0 g, 5.81 mmol) inethanol (50 mL) was added 50% by wt. hydroxylamine aqueous solution (1.0mL, 15.2 mmol). The reaction mixture was stirred at room temperature for3 h. The mixture was concentrated under reduced pressure to give a waxyoil, which was purified by silica gel chromatography to afford the[C(E)]-4-(1H-pyrazol-1-yl)benzaldehyde oxime as a white solid (923 mg).Then to a solution of the [C(E)]-4-(1H-pyrazol-1-yl)benzaldehyde oxime(923 mg, 4.94 mmol) and1,3-dichloro-5-(1-trifluoromethyl)ethenyl]benzene (i.e. the product fromExample 1, Step A) (1.31 g, 5.44 mmol) in tetrahydrofuran (25 mL) wasadded aqueous sodium hypochlorite solution (25 mL). After stirringovernight at room temperature, the reaction mixture was partitionedbetween ethyl acetate and water, and the aqueous extract was extractedfurther with ethyl acetate two times. The organic extracts werecombined, dried (MgSO₄) and concentrated, and the residual solid waspurified by silica gel chromatography and eluted with a gradient of0-50% ethyl acetate in hexane to afford the title product, a compound ofthe present invention, as a white solid (617 mg), m.p. 174-175° C.

¹H NMR (DMSO-d₆) δ 8.63 (d, 1H), 8.00 (d, 2H), 7.84 (m, 4H), 7.64 (d,2H), 6.60 (m, 1H), 4.38 (AB q, 2H).

Example 2 Preparation of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazoleStep A: Preparation of [C(E)]-4-fluoro-3-methylbenzaldehyde oxime

To a solution of 4-fluoro-3-methylbenzaldehyde (5.0 g, 36.2 mmol) inethanol (100 mL) was added 50% by wt. hydroxylamine aqueous solution(5.0 mL, 76.0 mmol). The reaction mixture was stirred at roomtemperature for 3 h. Then the mixture was concentrated under reducedpressure to give a waxy oil, which was purified by silica gelchromatography and eluted with a gradient of 0-25% ethyl acetate inhexane to afford the title compound as a white solid (4.971 g), m.p.79-80° C.

¹H NMR (CDCl₃) δ 8.08 (s, 1H), 7.51 (br s, 1H), 7.43 (d, 1H), 7.36 (m,1H), 7.01 (t, 1H), 2.29 (s, 3H).

Step B: Preparation of5-(3,5-dichlorophenyl)-3-(4-fluoro-3-methylphenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole

To a solution of [C(E)]-4-fluoro-3-methylbenzaldehyde oxime (i.e. theproduct of Step A) (4.971 g, 32.5 mmol),1,3-dichloro-5-(1-trifluoromethyl)ethenyl]benzene (i.e. the product fromExample 1, Step A) (8.684 g, 35.7 mmol); and tetrahydrofuran (200 mL)was added sodium hypochlorite aqueous solution (200 mL). After stilling1 h at room temperature, the reaction mixture was partitioned betweenethyl acetate and water, the aqueous extract was extracted further withethyl acetate two times. The organic extracts were combined, dried(MgSO₄), concentrated, and the residual solid was purified by silica gelchromatography and eluted with a gradient of 0-25% ethyl acetate inhexane to afford the title compound as a yellow waxy oil (10.515 g).

¹H NMR (CDCl₃) δ 7.52 (m, 3H), 7.45 (m, 1H), 7.41 (t, 1H), 7.05 (t, 1H),4.07 (d, 1H), 3.68 (d, 1H), 2.29 (s, 3H).

Step C: Preparation of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole

To a mixture of potassium carbonate (1.0 g, 7.24 mmol) and pyrazole(0.50 g, 7.35 mmol) in N,N-dimethylformamide (5 mL) was added5-(3,5-dichlorophenyl)-3-(4-fluoro-3-methylphenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole(i.e. the product from Step B) (0.50 g, 1.27 mmol). The reaction mixturewas stirred vigorously for 36 h at 120° C. Then the reaction mixture wasabsorbed onto silica gel, concentrated, and purified by flashchromatography on silica gel and eluted with a gradient of 0-25% ethylacetate in hexane to afford the title product, a compound of the presentinvention, as a yellow oil (32.0 mg).

¹H NMR (CDCl₃) δ 7.75 (d, 1H), 7.64 (d, 2H), 7.58 (dd, 1H), 7.52 (d,2H), 7.43 (m, 2H), 6.48 (t, 1H), 4.11 (d, 1H), 3.73 (d, 1H), 2.34 (s,3H).

Example 3 Preparation of2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]pyridineStep A: Preparation of [C(E)]-4-(2-pyridinyl)benzaldehyde oxime

A solution of 4-(pyridine-2-yl)benzaldehyde (1.83 g, 0.01 mol),hydroxylamine hydrochloride (0.7 g, 0.01 mol), and sodium acetate (0.33g) in ethanol (17 mL) and water (1 mL) was heated at reflux for 5 h. Thereaction mixture was cooled to room temperature, and the resultingprecipitate was collected, rinsed with ethanol, and dried under reducedpressure to afford 1.5 g of the title compound as a white solid.

¹H NMR (CDCl₃) δ 11.8 (br s, 1H), 8.8 (s, 8.4 (m, 3H), 8.3 (m, 1H), 7.8(m, 3H), 7.7 (m, 1H).

Step B: Preparation of2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]pyridine

To a solution of [C(E)]-4-(2-pyridinyl)benzaldehyde oxime (i.e. theproduct from Step A) (0.2 g, 0.001 mol) and1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the productfrom Example 1, Step A) (0.25 g, 0.001 mol) in dichloromethane (20 mL)at 5° C. was added an aqueous solution of sodium hypochlorite(6.15%—Clorox® brand) (5.5 mL) and triethylamine (6 drops). The mixturewas stirred at room temperature for 0.5 h, diluted with water (30 mL),and extracted with dichloromethane (2×20 mL). The organic extracts weredried (MgSO₄) and concentrated, under reduced pressure to provide asolid residue. The residue was purified by silica gel columnchromatography to afford 0.375 g of the title product, a compound of thepresent invention, as a white solid.

¹H NMR (CDCl₃) δ 8.8 (m, 1H), 8.05 (m, 2H), 7.8 (m, 3H), 7.76 (d, 2H),7.2 (d, 2H), 4.2 (d, 1H), 3.8 (d, 1H).

Example 4 Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(2-pyridinylmethyl)benzenesulfonamideStep A: Preparation of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-[(phenylmethyl)thio]phenyl]-5-(trifluoromethyl)isoxazole

To a solution of5-(3,5-dichlorophenyl)-3-(4-fluoro-3-methylphenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole(i.e. the product from Step B of Example 2) (2.6 g, 6.65 mmol) andpotassium carbonate (2.3 g, 16.6 mmol) in N,N-dimethylformamide (25 mL)was added benzyl mercaptan (0.782 mL, 6.65 mmol). The reaction mixturewas heated at 90° C. for 4 h. The reaction mixture was then cooled andexcess water was added, and the mixture was extracted with ethyl acetate(2×100 mL). The organic extracts were dried (MgSO₄) and concentratedunder reduced pressure to provide a solid residue. The elude product waspartially purified by silica gel column chromatography eluted withmixtures of hexane and ethyl acetate to afford a product containing thetitle compound (about 80% purity, 2.8 g).

¹H NMR (CDCl₃) δ 7.50 (s, 2H), 7.41 (s, 2H); 7.42 (m, 2H), 7.26-7.40 (m,7H), 4.16 (s, 2H), 4.1 (d, 1H), 3.65 (d, 1H).

Step B: Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzenesulfonylchloride

To a solution of5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-[(phenylmethyl)-thio]phenyl]-5-(trifluoromethyl)isoxazole(i.e. the product from Step A) (2.88 g, 5.8 mmol) in methylene chloride(50 mL) and water (50 mL) was added concentrated hydrochloride acid(1.92 mL, 20 mmol) at 5° C., followed by dropwise addition of sodiumhypochlorite (6.15%—Clorox® brand) (50 mL). The reaction mixture wasthen stirred vigorously for 1 h. The reaction mixture was added tomethylene chloride (100 mL) and washed with water (2×100 mL). Theorganic extracts were dried (MgSO₄) and concentrated to afford the titleproduct as an oil (3.1 g).

¹H NMR (CDCl₃) δ 8.15-7.3 (m, 6H), 4.1 (d, 1H), 3.7 (d, 1H), 2.83 (s,3H).

Step C: Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(2-pyridinylmethyl)benzenesulfonamide

To a solution of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzenesulfonylchloride (i.e. the product of Step B) (0.2 g, 0.42 mmol) in acetonitrile(20 mL) was added 2-(aminomethyl)pyridine (0.108 mL, 1.05 mmol). Thereaction mixture was heated to reflux, and then allowed to stir atambient temperature for 0.5 h. The mixture was then concentrated todryness and the crude product was purified by silica gel chromatographyusing hexane:ethyl acetate (80:20) as eluent. The isolated product wastriturated with a mixture of ether and hexane to afford the titleproduct, a compound of the present invention, as a white solid (59 mg),m.p. 57-58° C.

¹H NMR (CDCl₃) δ 8.47 (d, 1H), 8.04 (d, 1H), 7.50-7.6 (m, 5H), 7.43 (s,1H), 7.16 (m, 1H), 7.09 (d, 1H), 6.24 (br t, 1H), 4.23 (d, 1H), 4.04 (d,1H), 3.71 (d, 1H), 2.70 (s, 1H).

Example 5 Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylthio)benzonitrile

To a stirred suspension of sodium thiomethoxide (0.21 g, 3 mmol) andpotassium carbonate (0.28 g, 2 mmol) in 4 mL of N,N-dimethylformamidewas added a solution of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-fluorobenzonitrile(prepared by a method similar to Example 2, Step A and Step B; 1.00 g,2.48 mmol) in N,N-dimethylformamide (6 mL). This mixture was stirred atambient temperature for 1 h. Then an additional portion of sodiumthiomethoxide (0.21 g, 3 mmol) was added. After an additional 15minutes, water was added, and the mixture was successively extractedwith diethyl ether and ethyl acetate. The organic extracts were combinedand washed several times with water and saturated aqueous sodiumchloride solution, and then dried over magnesium sulfate, andconcentrated to leave an off-white solid. The solid was triturated witha mixture of diethyl ether and hexanes, collected on a glass frit, anddried in air to afford the title compound, a compound of the presentinvention, as a white solid (1.04 g).

¹H NMR (acetone-d₆) δ 8.0-8.1 (m, 2H), 7.66 (s, 2H), 7.62 (s, 1H), 7.6(m, 1H), 4.45 (d, 1H), 4.29 (d, 1H).

Example 6 Preparation of5-[(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylsulfonyl)benzonitrile

To a solution of5-[(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylthio)benzonitrile(i.e. the product of Example 5) (0.42 g, 1.0 mmol) in 20 mL ofdichloromethane was added 3-chloroperoxybenzoic acid (0.90 g of ˜77%peracid, 4.0 mmol) in one portion, and the mixture was stirred atambient temperature overnight. Aqueous sodium bisulfite solution wasadded, and after several minutes solid potassium carbonate was added.The layers were separated, and the organic phase was dried overmagnesium sulfate and concentrated to leave a solid. The solid wastriturated with a mixture of diethyl ether and hexanes, collected on aglass frit, and dried in air to afford the title product, a compound ofthe present invention, as a white solid (0.38 g).

¹H NMR (acetone-d₆) δ 8.42 (s, 1H), 8.38 (m, 1H), 8.26 (m, 1H), 7.67 (s,3H), 4.59 (d, 1H), 4.41 (d, 1H), 3.39 (s, 3H).

Example 7 Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)isoxazoleStep A: Preparation of3-(4-bromophenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole

To a solution of 4-bromobenzaldehyde (3.70 g, 20 mmol) in ethanol (30mL) was added 50% aqueous hydroxylamine (1.25 mL, 21 mmol) and glacialacetic acid (1.25 mL, 21 mmol). After 30 minutes, the reaction mixturewas diluted with ethyl acetate and washed with water and with saturatedaqueous sodium chloride solution, dried over magnesium sulfate, andconcentrated to leave a white solid. To a solution of this solid intetrahydrofuran (80 mL) and1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the productfrom Example 1, Step A) (4.82 g, 20 mmol) was added an aqueous solutionof sodium hypochlorite (6.15%—Clorox® brand) (80 mL) dropwise over 1 h.The reaction mixture was stirred at ambient temperature for 16 h. Thephases were separated, and the aqueous phase was extracted once withdiethyl ether. The combined organic phases were washed with saturatedaqueous sodium bisulfite solution and saturated aqueous sodium chloridesolution, and dried over magnesium sulfate, and concentrated to leave awhite solid. This solid was triturated with warm (40° C.) hexanes,allowed to cool, and solids were collected on a glass frit and dried toobtain the title product as a white solid (5.25 g).

¹H NMR (CDCl₃) δ 7.5-7.6 (m, 6H), 7.43 (s, 1H), 4.06 (d, 1H), 3.68 (d,1H)

Step B: Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(methylsulfonyl)-phenyl]-5-(trifluoromethyl)isoxazole

To a solution of3-(4-bromophenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole(i.e. the product of Step A) (4.39 mg, 1.00 mmol) in tetrahydrofuran (10mL) cooled below −75° C. was added a solution of n-butyllithium (2.5 Msolution in hexanes) dropwise over three minutes, while maintaining thetemperature at or below −72° C. Within one minute, S-methylmethanesulfonothioate (0.11 mL, 1.2 mmol) was added dropwise. Thereaction mixture was allowed to stir and warm slowly to ambienttemperature, and then it was poured into 1 N aqueous sodium hydroxidesolution, and the mixture was extracted with ethyl acetate. The organicphase was washed with saturated aqueous sodium chloride solution, driedover magnesium sulfate, and concentrated. The residue was subjected tochromatography on silica gel eluted with 10% ethyl acetate in hexanes.The isolated material was redissolved in dichloromethane (5 mL), treatedwith 3-chloroperoxybenzoic acid (˜77%, 0.39 g, 1.7 mmol) and allowed tostir at ambient temperature for 64 h. Additional 3-chloroperoxybenzoicacid (˜77%, 0.27 g, 1.2 mmol) was added, and the mixture was stirred for4 h. To this mixture was added saturated aqueous sodium bisulfitesolution, and then solid potassium carbonate was added carefully untilgas evolution ceased. The phases were separated, and the organic phasewas washed with 1 N aqueous sodium hydroxide solution and with saturatedaqueous sodium chloride solution, dried over magnesium sulfate, andconcentrated. The residue was triturated with diethyl ether and hexanesto obtain a solid which was collected on a glass frit. The solid waswashed with a mixture of diether and hexanes, and dried to afford thetitle product (0.12 g), a compound of the present invention.

¹H NMR (DMSO-d₆) δ 8.06 (m, 2H), 7.98 (m, 2H), 7.81 (s, 1H), 7.64 (m,2H), 4.43 (d, 1H), 4.37 (d, 1H), 3.27 (s, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 13 can be prepared. Thefollowing abbreviations are used in the Tables which follow: —CN meanscyano, —NO₂ means nitro, 2-Py means 2-pyridinyl, Ph means phenyl, Memeans methyl, Et means ethyl, Pr means propyl, n means normal, i meansiso, c means cyclo, i-Pr means isopropyl, c-Pr means cyclopropyl.

TABLE 1

wherein k is 1, 2, 3, 4 or 5. (R²)_(k) X¹ X² J¹ J² (R²)_(k) X¹ X² J¹ J²3-Cl, 4-Cl N CH H H 3-Cl, 5-Cl N CH H H 3-Cl, 4-Cl N CH Cl H 3-Cl, 5-ClN CH Cl H 3-Cl, 4-Cl N CH Br H 3-Cl, 5-Cl N CH Br H 3-Cl, 4-Cl N CH CF₃H 3-Cl, 5-Cl N CH CF₃ H 3-Cl, 4-Cl N CH —CN H 3-Cl, 5-Cl N CH —CN H3-Cl, 4-Cl N CH CONHMe H 3-Cl, 5-Cl N CH CONHMe H 3-Cl, 4-Cl N CH Me H3-Cl, 5-Cl N CH Me H 3-Cl, 4-Cl N CH Ph H 3-Cl, 5-Cl N CH Ph H 3-Cl,4-Cl N CH H CO₂Me 3-Cl, 5-Cl N CH H CO₂Me 3-Cl, 4-Cl N CH H CONHMe 3-Cl,5-Cl N CH H CONHMe 3-Cl, 4-Cl N CH CF₃ CO₂Me 3-Cl, 5-Cl N CH CF₃ CO₂Me3-Cl, 4-Cl N CH CF₃ CONHMe 3-Cl, 5-Cl N CH CF₃ CONHMe 3-Cl, 4-Cl N CH ClCO₂Me 3-Cl, 5-Cl N CH Cl CO₂Me 3-Cl, 4-Cl N CH Cl CONHMe 3-Cl, 5-Cl N CHCl CONHMe 3-Cl, 4-Cl N CH Br CO₂Me 3-Cl, 5-Cl N CH Br CO₂Me 3-Cl, 4-Cl NCH Br CONHMe 3-Cl, 5-Cl N CH Br CONHMe 3-Cl, 4-Cl N C—Cl H H 3-Cl, 5-ClN C—Cl H H 3-Cl, 4-Cl N C—Cl Cl H 3-Cl, 5-Cl N C—Cl Cl H 3-Cl, 4-Cl NC—Cl Br H 3-Cl, 5-Cl N C—Cl Br H 3-Cl, 4-Cl N C—Cl CF₃ H 3-Cl, 5-Cl NC—Cl CF₃ H 3-Cl, 4-Cl N C—Cl —CN H 3-Cl, 5-Cl N C—Cl —CN H 3-Cl, 4-Cl NC—Cl CONHMe H 3-Cl, 5-Cl N C—Cl CONHMe H 3-Cl, 4-Cl N C—Cl Me H 3-Cl,5-Cl N C—Cl Me H 3-Cl, 4-Cl N C—Cl Ph H 3-Cl, 5-Cl N C—Cl Ph H 3-Cl,4-Cl N C—Cl H CO₂Me 3-Cl, 5-Cl N C—Cl H CO₂Me 3-Cl, 4-Cl N C—Cl H CONHMe3-Cl, 5-Cl N C—Cl H CONHMe 3-Cl, 4-Cl N C—Cl CF₃ CO₂Me 3-Cl, 5-Cl N C—ClCF₃ CO₂Me 3-Cl, 4-Cl N C—Cl CF₃ CONHMe 3-Cl, 5-Cl N C—Cl CF₃ CONHMe3-Cl, 4-Cl N C—Cl Cl CO₂Me 3-Cl, 5-Cl N C—Cl Cl CO₂Me 3-Cl, 4-Cl N C—ClCl CONHMe 3-Cl, 5-Cl N C—Cl Cl CONHMe 3-Cl, 4-Cl N C—Cl Br CO₂Me 3-Cl,5-Cl N C—Cl Br CO₂Me 3-Cl, 4-Cl N C—Cl Br CONHMe 3-Cl, 5-Cl N C—Cl BrCONHMe 3-Cl, 4-Cl CH N H H 3-Cl, 5-Cl CH N H H 3-Cl, 4-Cl CH N Me H3-Cl, 5-Cl CH N Me H 3-Cl, 4-Cl CH N Ph H 3-Cl, 5-Cl CH N Ph H 3-Cl,4-Cl CH N Cl H 3-Cl, 5-Cl CH N Cl H 3-Cl, 4-Cl CH N Br H 3-Cl, 5-Cl CH NBr H 3-Cl, 4-Cl CH N —CN H 3-Cl, 5-Cl CH N —CN H 3-Cl, 4-Cl CH N CO₂Me H3-Cl, 5-Cl CH N CO₂Me H 3-Cl, 4-Cl CH N CONHMe H 3-Cl, 5-Cl CH N CONHMeH 3-Cl, 4-Cl CH N H Me 3-Cl, 5-Cl CH N H Me 3-Cl, 4-Cl CH N H Et 3-Cl,5-Cl CH N H Et 3-Cl, 4-Cl CH N H Pr 3-Cl, 5-Cl CH N H Pr 3-Cl, 4-Cl CH NH Ph 3-Cl, 5-Cl CH N H Ph 3-Cl, 4-Cl CH N H NO₂ 3-Cl, 5-Cl CH N H NO₂3-Cl, 4-Cl CH N Me Me 3-Cl, 5-Cl CH N Me Me 3-Cl, 4-Cl N N Br CO₂Me3-Cl, 5-Cl N N Br CO₂Me 3-Cl, 4-Cl N N Br CONHMe 3-Cl, 5-Cl N N BrCONHMe 3-Cl, 4-Cl N N H H 3-Cl, 5-Cl N N H H 3-Cl, 4-Cl N N Cl H 3-Cl,5-Cl N N Cl H 3-Cl, 4-Cl N N Br H 3-Cl, 5-Cl N N Br H 3-Cl, 4-Cl N N —CNH 3-Cl, 5-Cl N N —CN H 3-Cl, 4-Cl N N —NO₂ H 3-Cl, 5-Cl N N —NO₂ H 3-Cl,4-Cl N N SMe H 3-Cl, 5-Cl N N SMe H 3-Cl, 4-Cl N N CO₂Me H 3-Cl, 5-Cl NN CO₂Me H 3-Cl, 4-Cl N N Me H 3-Cl, 5-Cl N N Me H 3-Cl, 4-Cl N N Ph H3-Cl, 5-Cl N N Ph H H N CH H H H CH N H H 2-Cl N CH H H 2-Cl CH N H H3-Cl N CH H H 3-Cl CH N H H 4-Cl N CH H H 4-Cl CH N H H 2-Cl, 4-Cl N CHH H 2-Cl, 4-Cl CH N H H 2-F N CH H H 2-F CH N H H 3-F N CH H H 3-F CH NH H 4-F N CH H H 4-F CH N H H 2-F, 4-F N CH H H 2-F, 4-F CH N H H 3-F,4-F N CH H H 3-F, 4-F CH N H H 3-F, 5-F N CH H H 3-F, 5-F CH N H H 3-CF₃N CH H H 3-CF₃ CH N H H 4-CF₃ N CH H H 4-CF₃ CH N H H 3-CF₃, 5-CF₃ N CHH H 3-CF₃, 5-CF₃ CH N H H 3-Br N CH H H 3-Br CH N H H 4-Br N CH H H 4-BrCH N H H 3-I N CH H H 3-I CH N H H 4-I N CH H H 4-I CH N H H 3-CN N CH HH 3-CN CH N H H 4-CN N CH H H 4-CN CH N H H 3-Me N CH H H 3-Me CH N H H4-Me N CH H H 4-Me CH N H H 3-OMe N CH H H 3-OMe CH N H H 4-OMe N CH H H4-OMe CH N H H H N N H H 4-CF₃ N N H H 2-Cl N N H H 3-CF₃, 5-CF₃ N N H H3-Cl N N H H 3-Br N N H H 4-Cl N N H H 4-Br N N H H 2-Cl, 4-Cl N N H H3-I N N H H 2-F N N H H 4-I N N H H 3-F N N H H 3-CN N N H H 4-F N N H H4-CN N N H H 2-F, 4-F N N H H 3-Me N N H H 3-F, 4-F N N H H 4-Me N N H H3-F, 5-F N N H H 3-OMe N N H H 3-CF₃ N N H H 4-OMe N N H H

TABLE 2

wherein k is 1, 2, 3, 4 or 5. (R²)_(k) X¹ X² J¹ J² (R²)_(k) X¹ X² J¹ J²3-Cl, 4-Cl N CH H H 3-Cl, 5-Cl N CH H H 3-Cl, 4-Cl N CH Cl H 3-Cl, 5-ClN CH Cl H 3-Cl, 4-Cl N CH Br H 3-Cl, 5-Cl N CH Br H 3-Cl, 4-Cl N CH CF₃H 3-Cl, 5-Cl N CH CF₃ H 3-Cl, 4-Cl N CH —CN H 3-Cl, 5-Cl N CH —CN H3-Cl, 4-Cl N CH CONHMe H 3-Cl, 5-Cl N CH CONHMe H 3-Cl, 4-Cl N CH Me H3-Cl, 5-Cl N CH Me H 3-Cl, 4-Cl N CH Ph H 3-Cl, 5-Cl N CH Ph H 3-Cl,4-Cl N CH H CO₂Me 3-Cl, 5-Cl N CH H CO₂Me 3-Cl, 4-Cl N CH H CONHMe 3-Cl,5-Cl N CH H CONHMe 3-Cl, 4-Cl N CH CF₃ CO₂Me 3-Cl, 5-Cl N CH CF₃ CO₂Me3-Cl, 4-Cl N CH CF₃ CONHMe 3-Cl, 5-Cl N CH CF₃ CONHMe 3-Cl, 4-Cl N CH ClCO₂Me 3-Cl, 5-Cl N CH Cl CO₂Me 3-Cl, 4-Cl N CH Cl CONHMe 3-Cl, 5-Cl N CHCl CONHMe 3-Cl, 4-Cl N CH Br CO₂Me 3-Cl, 5-Cl N CH Br CO₂Me 3-Cl, 4-Cl NCH Br CONHMe 3-Cl, 5-Cl N CH Br CONHMe 3-Cl, 4-Cl N C—Cl H H 3-Cl, 5-ClN C—Cl H H 3-Cl, 4-Cl N C—Cl Cl H 3-Cl, 5-Cl N C—Cl Cl H 3-Cl, 4-Cl NC—Cl Br H 3-Cl, 5-Cl N C—Cl Br H 3-Cl, 4-Cl N C—Cl CF₃ H 3-Cl, 5-Cl NC—Cl CF₃ H 3-Cl, 4-Cl N C—Cl —CN H 3-Cl, 5-Cl N C—Cl —CN H 3-Cl, 4-Cl NC—Cl CONHMe H 3-Cl, 5-Cl N C—Cl CONHMe H 3-Cl, 4-Cl N C—Cl Me H 3-Cl,5-Cl N C—Cl Me H 3-Cl, 4-Cl N C—Cl Ph H 3-Cl, 5-Cl N C—Cl Ph H 3-Cl,4-Cl N C—Cl H CO₂Me 3-Cl, 5-Cl N C—Cl H CO₂Me 3-Cl, 4-Cl N C—Cl H CONHMe3-Cl, 5-Cl N C—Cl H CONHMe 3-Cl, 4-Cl N C—Cl CF₃ CO₂Me 3-Cl, 5-Cl N C—ClCF₃ CO₂Me 3-Cl, 4-Cl N C—Cl CF₃ CONHMe 3-Cl, 5-Cl N C—Cl CF₃ CONHMe3-Cl, 4-Cl N C—Cl Cl CO₂Me 3-Cl, 5-Cl N C—Cl Cl CO₂Me 3-Cl, 4-Cl N C—ClCl CONHMe 3-Cl, 5-Cl N C—Cl Cl CONHMe 3-Cl, 4-Cl N C—Cl Br CO₂Me 3-Cl,5-Cl N C—Cl Br CO₂Me 3-Cl, 4-Cl N C—Cl Br CONHMe 3-Cl, 5-Cl N C—Cl BrCONHMe 3-Cl, 4-Cl CH N H H 3-Cl, 5-Cl CH N H H 3-Cl, 4-Cl CH N Me H3-Cl, 5-Cl CH N Me H 3-Cl, 4-Cl CH N Ph H 3-Cl, 5-Cl CH N Ph H 3-Cl,4-Cl CH N Cl H 3-Cl, 5-Cl CH N Cl H 3-Cl, 4-Cl CH N Br H 3-Cl, 5-Cl CH NBr H 3-Cl, 4-Cl CH N —CN H 3-Cl, 5-Cl CH N —CN H 3-Cl, 4-Cl CH N CO₂Me H3-Cl, 5-Cl CH N CO₂Me H 3-Cl, 4-Cl CH N CONHMe H 3-Cl, 5-Cl CH N CONHMeH 3-Cl, 4-Cl CH N H Me 3-Cl, 5-Cl CH N H Me 3-Cl, 4-Cl CH N H Et 3-Cl,5-Cl CH N H Et 3-Cl, 4-Cl CH N H n-Pr 3-Cl, 5-Cl CH N H n-Pr 3-Cl, 4-ClCH N H Ph 3-Cl, 5-Cl CH N H Ph 3-Cl, 4-Cl CH N H NO₂ 3-Cl, 5-Cl CH N HNO₂ 3-Cl, 4-Cl CH N Me Me 3-Cl, 5-Cl CH N Me Me 3-Cl, 4-Cl N N Br CO₂Me3-Cl, 5-Cl N N Br CO₂Me 3-Cl, 4-Cl N N Br CONHMe 3-Cl, 5-Cl N N BrCONHMe 3-Cl, 4-Cl N N H H 3-Cl, 5-Cl N N H H 3-Cl, 4-Cl N N Cl H 3-Cl,5-Cl N N Cl H 3-Cl, 4-Cl N N Br H 3-Cl, 5-Cl N N Br H 3-Cl, 4-Cl N N —CNH 3-Cl, 5-Cl N N —CN H 3-Cl, 4-Cl N N —NO₂ H 3-Cl, 5-Cl N N —NO₂ H 3-Cl,4-Cl N N SMe H 3-Cl, 5-Cl N N SMe H 3-Cl, 4-Cl N N CO₂Me H 3-Cl, 5-Cl NN CO₂Me H 3-Cl, 4-Cl N N Me H 3-Cl, 5-Cl N N Me H 3-Cl, 4-Cl N N Ph H3-Cl, 5-Cl N N Ph H H N CH H H H CH N H H 2-Cl N CH H H 2-Cl CH N H H3-Cl N CH H H 3-Cl CH N H H 4-Cl N CH H H 4-Cl CH N H H 2-Cl, 4-Cl N CHH H 2-Cl, 4-Cl CH N H H 2-F N CH H H 2-F CH N H H 3-F N CH H H 3-F CH NH H 4-F N CH H H 4-F CH N H H 2-F, 4-F N CH H H 2-F, 4-F CH N H H 3-F,4-F N CH H H 3-F, 4-F CH N H H 3-F, 5-F N CH H H 3-F, 5-F CH N H H 3-CF₃N CH H H 3-CF₃ CH N H H 4-CF₃ N CH H H 4-CF₃ CH N H H 3-CF₃, 5-CF₃ N CHH H 3-CF₃, 5-CF₃ CH N H H 3-Br N CH H H 3-Br CH N H H 4-Br N CH H H 4-BrCH N H H 3-I N CH H H 3-I CH N H H 4-I N CH H H 4-I CH N H H 3-CN N CH HH 3-CN CH N H H 4-CN N CH H H 4-CN CH N H H 3-Me N CH H H 3-Me CH N H H4-Me N CH H H 4-Me CH N H H 3-OMe N CH H H 3-OMe CH N H H 4-OMe N CH H H4-OMe CH N H H H N N H H 4-CF₃ N N H H 2-Cl N N H H 3-CF₃, 5-CF₃ N N H H3-Cl N N H H 3-Br N N H H 4-Cl N N H H 4-Br N N H H 2-Cl, 4-Cl N N H H3-I N N H H 2-F N N H H 4-I N N H H 3-F N N H H 3-CN N N H H 4-F N N H H4-CN N N H H 2-F, 4-F N N H H 3-Me N N H H 3-F, 4-F N N H H 4-Me N N H H3-F, 5-F N N H H 3-OMe N N H H 3-CF₃ N N H H 4-OMe N N H H

TABLE 3

wherein k is 1, 2, 3, 4 or 5. (R²)_(k) X¹ X² J¹ J² (R²)_(k) X¹ X² J¹ J²3-Cl, 4-Cl N CH H H 3-Cl, 5-Cl N CH H H 3-Cl, 4-Cl N CH Cl H 3-Cl, 5-ClN CH Cl H 3-Cl, 4-Cl N CH Br H 3-Cl, 5-Cl N CH Br H 3-Cl, 4-Cl N CH CF₃H 3-Cl, 5-Cl N CH CF₃ H 3-Cl, 4-Cl N CH —CN H 3-Cl, 5-Cl N CH —CN H3-Cl, 4-Cl N CH CONHMe H 3-Cl, 5-Cl N CH CONHMe H 3-Cl, 4-Cl N CH Me H3-Cl, 5-Cl N CH Me H 3-Cl, 4-Cl N CH Ph H 3-Cl, 5-Cl N CH Ph H 3-Cl,4-Cl N CH H CO₂Me 3-Cl, 5-Cl N CH H CO₂Me 3-Cl, 4-Cl N CH H CONHMe 3-Cl,5-Cl N CH H CONHMe 3-Cl, 4-Cl N CH CF₃ CO₂Me 3-Cl, 5-Cl N CH CF₃ CO₂Me3-Cl, 4-Cl N CH CF₃ CONHMe 3-Cl, 5-Cl N CH CF₃ CONHMe 3-Cl, 4-Cl N CH ClCO₂Me 3-Cl, 5-Cl N CH Cl CO₂Me 3-Cl, 4-Cl N CH Cl CONHMe 3-Cl, 5-Cl N CHCl CONHMe 3-Cl, 4-Cl N CH Br CO₂Me 3-Cl, 5-Cl N CH Br CO₂Me 3-Cl, 4-Cl NCH Br CONHMe 3-Cl, 5-Cl N CH Br CONHMe 3-Cl, 4-Cl N C—Cl H H 3-Cl, 5-ClN C—Cl H H 3-Cl, 4-Cl N C—Cl Cl H 3-Cl, 5-Cl N C—Cl Cl H 3-Cl, 4-Cl NC—Cl Br H 3-Cl, 5-Cl N C—Cl Br H 3-Cl, 4-Cl N C—Cl CF₃ H 3-Cl, 5-Cl NC—Cl CF₃ H 3-Cl, 4-Cl N C—Cl —CN H 3-Cl, 5-Cl N C—Cl —CN H 3-Cl, 4-Cl NC—Cl CONHMe H 3-Cl, 5-Cl N C—Cl CONHMe H 3-Cl, 4-Cl N C—Cl Me H 3-Cl,5-Cl N C—Cl Me H 3-Cl, 4-Cl N C—Cl Ph H 3-Cl, 5-Cl N C—Cl Ph H 3-Cl,4-Cl N C—Cl H CO₂Me 3-Cl, 5-Cl N C—Cl H CO₂Me 3-Cl, 4-Cl N C—Cl H CONHMe3-Cl, 5-Cl N C—Cl H CONHMe 3-Cl, 4-Cl N C—Cl CF₃ CO₂Me 3-Cl, 5-Cl N C—ClCF₃ CO₂Me 3-Cl, 4-Cl N C—Cl CF₃ CONHMe 3-Cl, 5-Cl N C—Cl CF₃ CONHMe3-Cl, 4-Cl N C—Cl Cl CO₂Me 3-Cl, 5-Cl N C—Cl Cl CO₂Me 3-Cl, 4-Cl N C—ClCl CONHMe 3-Cl, 5-Cl N C—Cl Cl CONHMe 3-Cl, 4-Cl N C—Cl Br CO₂Me 3-Cl,5-Cl N C—Cl Br CO₂Me 3-Cl, 4-Cl N C—Cl Br CONHMe 3-Cl, 5-Cl N C—Cl BrCONHMe 3-Cl, 4-Cl CH N H H 3-Cl, 5-Cl CH N H H 3-Cl, 4-Cl CH N Me H3-Cl, 5-Cl CH N Me H 3-Cl, 4-Cl CH N Ph H 3-Cl, 5-Cl CH N Ph H 3-Cl,4-Cl CH N Cl H 3-Cl, 5-Cl CH N Cl H 3-Cl, 4-Cl CH N Br H 3-Cl, 5-Cl CH NBr H 3-Cl, 4-Cl CH N —CN H 3-Cl, 5-Cl CH N —CN H 3-Cl, 4-Cl CH N CO₂Me H3-Cl, 5-Cl CH N CO₂Me H 3-Cl, 4-Cl CH N CONHMe H 3-Cl, 5-Cl CH N CONHMeH 3-Cl, 4-Cl CH N H Me 3-Cl, 5-Cl CH N H Me 3-Cl, 4-Cl CH N H Et 3-Cl,5-Cl CH N H Et 3-Cl, 4-Cl CH N H n-Pr 3-Cl, 5-Cl CH N H n-Pr 3-Cl, 4-ClCH N H Ph 3-Cl, 5-Cl CH N H Ph 3-Cl, 4-Cl CH N H NO₂ 3-Cl, 5-Cl CH N HNO₂ 3-Cl, 4-Cl CH N Me Me 3-Cl, 5-Cl CH N Me Me 3-Cl, 4-Cl N N Br CO₂Me3-Cl, 5-Cl N N Br CO₂Me 3-Cl, 4-Cl N N Br CONHMe 3-Cl, 5-Cl N N BrCONHMe 3-Cl, 4-Cl N N H H 3-Cl, 5-Cl N N H H 3-Cl, 4-Cl N N Cl H 3-Cl,5-Cl N N Cl H 3-Cl, 4-Cl N N Br H 3-Cl, 5-Cl N N Br H 3-Cl, 4-Cl N N —CNH 3-Cl, 5-Cl N N —CN H 3-Cl, 4-Cl N N NO₂ H 3-Cl, 5-Cl N N NO₂ H 3-Cl,4-Cl N N SMe H 3-Cl, 5-Cl N N SMe H 3-Cl, 4-Cl N N CO₂Me H 3-Cl, 5-Cl NN CO₂Me H 3-Cl, 4-Cl N N Me H 3-Cl, 5-Cl N N Me H 3-Cl, 4-Cl N N Ph H3-Cl, 5-Cl N N Ph H H N CH H H H CH N H H 2-Cl N CH H H 2-Cl CH N H H3-Cl N CH H H 3-Cl CH N H H 4-Cl N CH H H 4-Cl CH N H H 2-Cl, 4-Cl N CHH H 2-Cl, 4-Cl CH N H H 2-F N CH H H 2-F CH N H H 3-F N CH H H 3-F CH NH H 4-F N CH H H 4-F CH N H H 2-F, 4-F N CH H H 2-F, 4-F CH N H H 3-F,4-F N CH H H 3-F, 4-F CH N H H 3-F, 5-F N CH H H 3-F, 5-F CH N H H 3-CF₃N CH H H 3-CF₃ CH N H H 4-CF₃ N CH H H 4-CF₃ CH N H H 3-CF₃, 5-CF₃ N CHH H 3-CF₃, 5-CF₃ CH N H H 3-Br N CH H H 3-Br CH N H H 4-Br N CH H H 4-BrCH N H H 3-I N CH H H 3-I CH N H H 4-I N CH H H 4-I CH N H H 3-CN N CH HH 3-CN CH N H H 4-CN N CH H H 4-CN CH N H H 3-Me N CH H H 3-Me CH N H H4-Me N CH H H 4-Me CH N H H 3-OMe N CH H H 3-OMe CH N H H 4-OMe N CH H H4-OMe CH N H H H N N H H 4-CF₃ N N H H 2-Cl N N H H 3-CF₃, 5-CF₃ N N H H3-Cl N N H H 3-Br N N H H 4-Cl N N H H 4-Br N N H H 2-Cl, 4-Cl N N H H3-I N N H H 2-F N N H H 4-I N N H H 3-F N N H H 3-CN N N H H 4-F N N H H4-CN N N H H 2-F, 4-F N N H H 3-Me N N H H 3-F, 4-F N N H H 4-Me N N H H3-F, 5-F N N H H 3-OMe N N H H 3-CF₃ N N H H 4-OMe N N H H

TABLE 4

R¹ R² R³ X¹ X² A³ R¹ R² R³ X¹ X² A³ Me 4- H N CH CH CF₃ 4- H N CH N ClCl Me 5- H N CH CH CF₃ 5- H N CH N Cl Cl Me 4- H CH N CH CF₃ 4- H CH N NCl Cl Me 5- H CH N CH CF₃ 5- H CH N N Cl Cl Me 4- H N N CH CF₃ 4- H N NN Cl Cl Me 5- H N N CH CF₃ 5- H N N N Cl Cl Me 4- Me N CH CH CF₃ 4- Me NCH N Cl Cl Me 5- Me N CH CH CF₃ 5- Me N CH N Cl Cl Me 4- Me CH N CH CF₃4- Me CH N N Cl Cl Me 5- Me CH N CH CF₃ 5- Me CH N N Cl Cl Me 4- Me N NCH CF₃ 4- Me N N N Cl Cl Me 5- Me N N CH CF₃ 5- Me N N N Cl Cl Me 4- ClN CH CH CF₃ 4- Cl N CH N Cl Cl Me 5- Cl N CH CH CF₃ 5- Cl N CH N Cl ClMe 4- Cl CH N CH CF₃ 4- Cl CH N N Cl Cl Me 5- Cl CH N CH CF₃ 5- Cl CH NN Cl Cl Me 4- Cl N N CH CF₃ 4- Cl N N N Cl Cl Me 5- Cl N N CH CF₃ 5- ClN N N Cl Cl

TABLE 5

wherein k is 1, 2, 3, 4 or 5. R¹ (R²)_(k) R³ X³ X⁴ J³ J⁴ A³ CF₃ 3-Cl,4-Cl H CH S H H CH CF₃ 3-Cl, 4-Cl H CH O H H CH CF₃ 3-Cl, 4-Cl H CH NMeH H CH CF₃ 3-Cl, 4-Cl H N S H H CH CF₃ 3-Cl, 4-Cl H N O H H CH CF₃ 3-Cl,5-Cl H CH S H H CH CF₃ 3-Cl, 5-Cl H CH O H H CH CF₃ 3-Cl, 5-Cl H CH NMeH H CH CF₃ 3-Cl, 5-Cl H N S H H CH CF₃ 3-Cl, 5-Cl H N O H H CH CF₃ 3-Cl,4-Cl Me CH S H H CH CF₃ 3-Cl, 4-Cl Me CH O H H CH CF₃ 3-Cl, 4-Cl Me CHNMe H H CH CF₃ 3-Cl, 4-Cl Me N S H H CH CF₃ 3-Cl, 4-Cl Me N O H H CH CF₃3-Cl, 5-Cl Me CH S H H CH CF₃ 3-Cl, 5-Cl Me CH O H H CH CF₃ 3-Cl, 5-ClMe CH NMe H H CH CF₃ 3-Cl, 5-Cl Me N S H H CH CF₃ 3-Cl, 5-Cl Me N O H HCH CF₃ 3-Cl, 4-Cl H CH S H H N CF₃ 3-Cl, 4-Cl H CH O H H N CF₃ 3-Cl,4-Cl H CH NMe H H N CF₃ 3-Cl, 4-Cl H N S H H N CF₃ 3-Cl, 4-Cl H N O H HN CF₃ 3-Cl, 5-Cl H CH S H H N CF₃ 3-Cl, 5-Cl H CH O H H N CF₃ 3-Cl, 5-ClH CH NMe H H N CF₃ 3-Cl, 5-Cl H N S H H N CF₃ 3-Cl, 5-Cl H N O H H N Me3-Cl, 4-Cl H CH S H H CH Me 3-Cl, 4-Cl H CH O H H CH Me 3-Cl, 4-Cl H CHNMe H H CH Me 3-Cl, 4-Cl H N S H H CH Me 3-Cl, 4-Cl H N O H H CH Me3-Cl, 5-Cl H CH S H H CH Me 3-Cl, 5-Cl H CH O H H CH Me 3-Cl, 5-Cl H CHNMe H H CH Me 3-Cl, 5-Cl H N S H H CH Me 3-Cl, 5-Cl H N O H H CH CF₃3-Cl, 4-Cl H CH S Cl H CH CF₃ 3-Cl, 4-Cl H CH O Cl H CH CF₃ 3-Cl, 4-Cl HCH NMe Cl H CH CF₃ 3-Cl, 4-Cl H N S Cl H CH CF₃ 3-Cl, 4-Cl H N O Cl H CHCF₃ 3-Cl, 5-Cl H CH S Cl H CH CF₃ 3-Cl, 5-Cl H CH O Cl H CH CF₃ 3-Cl,5-Cl H CH NMe Cl H CH CF₃ 3-Cl, 5-Cl H N S Cl H CH CF₃ 3-Cl, 5-Cl H N OCl H CH CF₃ 3-Cl, 4-Cl H CH S Cl Cl CH CF₃ 3-Cl, 4-Cl H CH O Cl Cl CHCF₃ 3-Cl, 4-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 4-Cl H N S Cl Cl CH CF₃ 3-Cl,4-Cl H N O Cl Cl CH CF₃ 3-Cl, 5-Cl H CH S Cl Cl CH CF₃ 3-Cl, 5-Cl H CH OCl Cl CH CF₃ 3-Cl, 5-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 5-Cl H N S Cl Cl CHCF₃ 3-Cl, 5-Cl H N O Cl Cl CH

TABLE 6

wherein k is 1, 2, 3, 4 or 5. R¹ (R²)_(k) R³ X³ X⁴ J³ J⁴ A³ CF₃ 3-Cl,4-Cl H CH S H H CH CF₃ 3-Cl, 4-Cl H CH O H H CH CF₃ 3-Cl, 4-Cl H CH NMeH H CH CF₃ 3-Cl, 4-Cl H N S H H CH CF₃ 3-Cl, 4-Cl H N O H H CH CF₃ 3-Cl,5-Cl H CH S H H CH CF₃ 3-Cl, 5-Cl H CH O H H CH CF₃ 3-Cl, 5-Cl H CH NMeH H CH CF₃ 3-Cl, 5-Cl H N S H H CH CF₃ 3-Cl, 5-Cl H N O H H CH CF₃ 3-Cl,4-Cl Me CH S H H CH CF₃ 3-Cl, 4-Cl Me CH O H H CH CF₃ 3-Cl, 4-Cl Me CHNMe H H CH CF₃ 3-Cl, 4-Cl Me N S H H CH CF₃ 3-Cl, 4-Cl Me N O H H CH CF₃3-Cl, 5-Cl Me CH S H H CH CF₃ 3-Cl, 5-Cl Me CH O H H CH CF₃ 3-Cl, 5-ClMe CH NMe H H CH CF₃ 3-Cl, 5-Cl Me N S H H CH CF₃ 3-Cl, 5-Cl Me N O H HCH CF₃ 3-Cl, 4-Cl H CH S H H N CF₃ 3-Cl, 4-Cl H CH O H H N CF₃ 3-Cl,4-Cl H CH NMe H H N CF₃ 3-Cl, 4-Cl H N S H H N CF₃ 3-Cl, 4-Cl H N O H HN CF₃ 3-Cl, 5-Cl H CH S H H N CF₃ 3-Cl, 5-Cl H CH O H H N CF₃ 3-Cl, 5-ClH CH NMe H H N CF₃ 3-Cl, 5-Cl H N S H H N CF₃ 3-Cl, 5-Cl H N O H H N Me3-Cl, 4-Cl H CH S H H CH Me 3-Cl, 4-Cl H CH O H H CH Me 3-Cl, 4-Cl H CHNMe H H CH Me 3-Cl, 4-Cl H N S H H CH Me 3-Cl, 4-Cl H N O H H CH Me3-Cl, 5-Cl H CH S H H CH Me 3-Cl, 5-Cl H CH O H H CH Me 3-Cl, 5-Cl H CHNMe H H CH Me 3-Cl, 5-Cl H N S H H CH Me 3-Cl, 5-Cl H N O H H CH CF₃3-Cl, 4-Cl H CH S Cl H CH CF₃ 3-Cl, 4-Cl H CH O Cl H CH CF₃ 3-Cl, 4-Cl HCH NMe Cl H CH CF₃ 3-Cl, 4-Cl H N S Cl H CH CF₃ 3-Cl, 4-Cl H N O Cl H CHCF₃ 3-Cl, 5-Cl H CH S Cl H CH CF₃ 3-Cl, 5-Cl H CH O Cl H CH CF₃ 3-Cl,5-Cl H CH NMe Cl H CH CF₃ 3-Cl, 5-Cl H N S Cl H CH CF₃ 3-Cl, 5-Cl H N OCl H CH CF₃ 3-Cl, 4-Cl H CH S Cl Cl CH CF₃ 3-Cl, 4-Cl H CH O Cl Cl CHCF₃ 3-Cl, 4-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 4-Cl H N S Cl Cl CH CF₃ 3-Cl,4-Cl H N O Cl Cl CH CF₃ 3-Cl, 5-Cl H CH S Cl Cl CH CF₃ 3-Cl, 5-Cl H CH OCl Cl CH CF₃ 3-Cl, 5-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 5-Cl H N S Cl Cl CHCF₃ 3-Cl, 5-Cl H N O Cl Cl CH

TABLE 7

wherein k is 1, 2, 3, 4 or 5. R¹ (R²)_(k) R³ X³ X⁴ J³ J⁴ A³ CF₃ 3-Cl,4-Cl H CH S H H CH CF₃ 3-Cl, 4-Cl H CH O H H CH CF₃ 3-Cl, 4-Cl H CH NMeH H CH CF₃ 3-Cl, 4-Cl H N S H H CH CF₃ 3-Cl, 4-Cl H N O H H CH CF₃ 3-Cl,5-Cl H CH S H H CH CF₃ 3-Cl, 5-Cl H CH O H H CH CF₃ 3-Cl, 5-Cl H CH NMeH H CH CF₃ 3-Cl, 5-Cl H N S H H CH CF₃ 3-Cl, 5-Cl H N O H H CH CF₃ 3-Cl,4-Cl Me CH S H H CH CF₃ 3-Cl, 4-Cl Me CH O H H CH CF₃ 3-Cl, 4-Cl Me CHNMe H H CH CF₃ 3-Cl, 4-Cl Me N S H H CH CF₃ 3-Cl, 4-Cl Me N O H H CH CF₃3-Cl, 5-Cl Me CH S H H CH CF₃ 3-Cl, 5-Cl Me CH O H H CH CF₃ 3-Cl, 5-ClMe CH NMe H H CH CF₃ 3-Cl, 5-Cl Me N S H H CH CF₃ 3-Cl, 5-Cl Me N O H HCH CF₃ 3-Cl, 4-Cl H CH S H H N CF₃ 3-Cl, 4-Cl H CH O H H N CF₃ 3-Cl,4-Cl H CH NMe H H N CF₃ 3-Cl, 4-Cl H N S H H N CF₃ 3-Cl, 4-Cl H N O H HN CF₃ 3-Cl, 5-Cl H CH S H H N CF₃ 3-Cl, 5-Cl H CH O H H N CF₃ 3-Cl, 5-ClH CH NMe H H N CF₃ 3-Cl, 5-Cl H N S H H N CF₃ 3-Cl, 5-Cl H N O H H N Me3-Cl, 4-Cl H CH S H H CH Me 3-Cl, 4-Cl H CH O H H CH Me 3-Cl, 4-Cl H CHNMe H H CH Me 3-Cl, 4-Cl H N S H H CH Me 3-Cl, 4-Cl H N O H H CH Me3-Cl, 5-Cl H CH S H H CH Me 3-Cl, 5-Cl H CH O H H CH Me 3-Cl, 5-Cl H CHNMe H H CH Me 3-Cl, 5-Cl H N S H H CH Me 3-Cl, 5-Cl H N O H H CH CF₃3-Cl, 4-Cl H CH S Cl H CH CF₃ 3-Cl, 4-Cl H CH O Cl H CH CF₃ 3-Cl, 4-Cl HCH NMe Cl H CH CF₃ 3-Cl, 4-Cl H N S Cl H CH CF₃ 3-Cl, 4-Cl H N O Cl H CHCF₃ 3-Cl, 5-Cl H CH S Cl H CH CF₃ 3-Cl, 5-Cl H CH O Cl H CH CF₃ 3-Cl,5-Cl H CH NMe Cl H CH CF₃ 3-Cl, 5-Cl H N S Cl H CH CF₃ 3-Cl, 5-Cl H N OCl H CH CF₃ 3-Cl, 4-Cl H CH S Cl Cl CH CF₃ 3-Cl, 4-Cl H CH O Cl Cl CHCF₃ 3-Cl, 4-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 4-Cl H N S Cl Cl CH CF₃ 3-Cl,4-Cl H N O Cl Cl CH CF₃ 3-Cl, 5-Cl H CH S Cl Cl CH CF₃ 3-Cl, 5-Cl H CH OCl Cl CH CF₃ 3-Cl, 5-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 5-Cl H N S Cl Cl CHCF₃ 3-Cl, 5-Cl H N O Cl Cl CH

TABLE 8

wherein k is 1, 2, 3, 4 or 5. R¹ (R²)_(k) R³ X³ X⁴ J³ J⁴ A³ CF₃ 3-Cl,4-Cl H CH S H H CH CF₃ 3-Cl, 4-Cl H CH O H H CH CF₃ 3-Cl, 4-Cl H CH NMeH H CH CF₃ 3-Cl, 4-Cl H N S H H CH CF₃ 3-Cl, 4-Cl H N O H H CH CF₃ 3-Cl,5-Cl H CH S H H CH CF₃ 3-Cl, 5-Cl H CH O H H CH CF₃ 3-Cl, 5-Cl H CH NMeH H CH CF₃ 3-Cl, 5-Cl H N S H H CH CF₃ 3-Cl, 5-Cl H N O H H CH CF₃ 3-Cl,4-Cl Me CH S H H CH CF₃ 3-Cl, 4-Cl Me CH O H H CH CF₃ 3-Cl, 4-Cl Me CHNMe H H CH CF₃ 3-Cl, 4-Cl Me N S H H CH CF₃ 3-Cl, 4-Cl Me N O H H CH CF₃3-Cl, 5-Cl Me CH S H H CH CF₃ 3-Cl, 5-Cl Me CH O H H CH CF₃ 3-Cl, 5-ClMe CH NMe H H CH CF₃ 3-Cl, 5-Cl Me N S H H CH CF₃ 3-Cl, 5-Cl Me N O H HCH CF₃ 3-Cl, 4-Cl H CH S H H N CF₃ 3-Cl, 4-Cl H CH O H H N CF₃ 3-Cl,4-Cl H CH NMe H H N CF₃ 3-Cl, 4-Cl H N S H H N CF₃ 3-Cl, 4-Cl H N O H HN CF₃ 3-Cl, 5-Cl H CH S H H N CF₃ 3-Cl, 5-Cl H CH O H H N CF₃ 3-Cl, 5-ClH CH NMe H H N CF₃ 3-Cl, 5-Cl H N S H H N CF₃ 3-Cl, 5-Cl H N O H H N Me3-Cl, 4-Cl H CH S H H CH Me 3-Cl, 4-Cl H CH O H H CH Me 3-Cl, 4-Cl H CHNMe H H CH Me 3-Cl, 4-Cl H N S H H CH Me 3-Cl, 4-Cl H N O H H CH Me3-Cl, 5-Cl H CH S H H CH Me 3-Cl, 5-Cl H CH O H H CH Me 3-Cl, 5-Cl H CHNMe H H CH Me 3-Cl, 5-Cl H N S H H CH Me 3-Cl, 5-Cl H N O H H CH CF₃3-Cl, 4-Cl H CH S Cl H CH CF₃ 3-Cl, 4-Cl H CH O Cl H CH CF₃ 3-Cl, 4-Cl HCH NMe Cl H CH CF₃ 3-Cl, 4-Cl H N S Cl H CH CF₃ 3-Cl, 4-Cl H N O Cl H CHCF₃ 3-Cl, 5-Cl H CH S Cl H CH CF₃ 3-Cl, 5-Cl H CH O Cl H CH CF₃ 3-Cl,5-Cl H CH NMe Cl H CH CF₃ 3-Cl, 5-Cl H N S Cl H CH CF₃ 3-Cl, 5-Cl H N OCl H CH CF₃ 3-Cl, 4-Cl H CH S Cl Cl CH CF₃ 3-Cl, 4-Cl H CH O Cl Cl CHCF₃ 3-Cl, 4-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 4-Cl H N S Cl Cl CH CF₃ 3-Cl,4-Cl H N O Cl Cl CH CF₃ 3-Cl, 5-Cl H CH S Cl Cl CH CF₃ 3-Cl, 5-Cl H CH OCl Cl CH CF₃ 3-Cl, 5-Cl H CH NMe Cl Cl CH CF₃ 3-Cl, 5-Cl H N S Cl Cl CHCF₃ 3-Cl, 5-Cl H N O Cl Cl CH

TABLE 9

wherein k is 1, 2, 3, 4 or 5. R¹ (R²)_(k) R³ A³ X⁵ X⁶ X⁷ CF₃ 3-Cl, 4-ClH CH CH CH CH CF₃ 3-Cl, 4-Cl H CH C—Cl CH CH CF₃ 3-Cl, 4-Cl H CH C—Me CHCH CF₃ 3-Cl, 4-Cl H CH C—F CH CH CF₃ 3-Cl, 4-Cl H CH C—CO₂Me CH CH CF₃3-Cl, 4-Cl H CH C—CONHMe CH CH CF₃ 3-Cl, 4-Cl H CH CH C—Cl CH CF₃ 3-Cl,4-Cl H CH CH C—Me CH CF₃ 3-Cl, 4-Cl H CH CH C—F CH CF₃ 3-Cl, 4-Cl H CHCH C—CO₂Me CH CF₃ 3-Cl, 4-Cl H CH CH C—CONHMe CH CF₃ 3-Cl, 5-Cl H CH CHCH CH CF₃ 3-Cl, 5-Cl H CH C—Cl CH CH CF₃ 3-Cl, 5-Cl H CH C—Me CH CH CF₃3-Cl, 5-Cl H CH C—F CH CH CF₃ 3-Cl, 5-Cl H CH C—CO₂Me CH CH CF₃ 3-Cl,5-Cl H CH C—CONHMe CH CH CF₃ 3-Cl, 5-Cl H CH CH C—Cl CH CF₃ 3-Cl, 5-Cl HCH CH C—Me CH CF₃ 3-Cl, 5-Cl H CH CH C—F CH CF₃ 3-Cl, 5-Cl H CH CHC—CO₂Me CH CF₃ 3-Cl, 5-Cl H CH CH C—CONHMe CH CF₃ 3-Cl, 4-Cl Me CH CH CHCH CF₃ 3-Cl, 4-Cl Me CH C—Cl CH CH CF₃ 3-Cl, 4-Cl Me CH C—Me CH CH CF₃3-Cl, 4-Cl Me CH C—F CH CH CF₃ 3-Cl, 4-Cl Me CH C—CO₂Me CH CH CF₃ 3-Cl,4-Cl Me CH C—CONHMe CH CH CF₃ 3-Cl, 4-Cl Me CH CH C—Cl CH CF₃ 3-Cl, 4-ClMe CH CH C—Me CH CF₃ 3-Cl, 4-Cl Me CH CH C—F CH CF₃ 3-Cl, 4-Cl Me CH CHC—CO₂Me CH CF₃ 3-Cl, 4-Cl Me CH CH C—CONHMe CH CF₃ 3-Cl, 5-Cl Me CH CHCH CH CF₃ 3-Cl, 5-Cl Me CH C—Cl CH CH CF₃ 3-Cl, 5-Cl Me CH C—Me CH CHCF₃ 3-Cl, 5-Cl Me CH C—F CH CH CF₃ 3-Cl, 5-Cl Me CH C—CO₂Me CH CH CF₃3-Cl, 5-Cl Me CH C—CONHMe CH CH CF₃ 3-Cl, 5-Cl Me CH CH C—Cl CH CF₃3-Cl, 5-Cl Me CH CH C—Me CH CF₃ 3-Cl, 5-Cl Me CH CH C—F CH CF₃ 3-Cl,5-Cl Me CH CH C—CO₂Me CH CF₃ 3-Cl, 5-Cl Me CH CH C—CONHMe CH CF₃ 3-Cl,4-Cl H CH N CH CH CF₃ 3-Cl, 4-Cl H CH CH N CH CF₃ 3-Cl, 4-Cl Me CH N CHCH CF₃ 3-Cl, 4-Cl Me CH CH N CH CF₃ 3-Cl, 4-Cl H CH N CH C—Cl CF₃ 3-Cl,4-Cl H CH CH N C—Cl CF₃ 3-Cl, 4-Cl H CH CH C—Cl N CF₃ 3-Cl, 4-Cl Me CH NCH C—Cl CF₃ 3-Cl, 4-Cl Me CH CH N C—Cl CF₃ 3-Cl, 4-Cl Me CH CH C—Cl NCF₃ 3-Cl, 5-Cl H CH N CH CH CF₃ 3-Cl, 5-Cl H CH CH N CH CF₃ 3-Cl, 5-ClMe CH N CH CH CF₃ 3-Cl, 5-Cl Me CH CH N CH CF₃ 3-Cl, 5-Cl H CH N CH C—ClCF₃ 3-Cl, 5-Cl H CH CH N C—Cl CF₃ 3-Cl, 5-Cl H CH CH C—Cl N CF₃ 3-Cl,5-Cl Me CH N CH C—Cl CF₃ 3-Cl, 5-Cl Me CH CH N C—Cl CF₃ 3-Cl, 5-Cl Me CHCH C—Cl N

TABLE 10

R¹ (R²)_(k) R³ A³ X⁸ X⁹ J⁵ CF₃ 3-Cl, 4-Cl H CH N CH H CF₃ 3-Cl, 4-Cl HCH N N H CF₃ 3-Cl, 4-Cl H CH N C—Cl H CF₃ 3-Cl, 4-Cl Me CH N CH H CF₃3-Cl, 4-Cl Me CH N N H CF₃ 3-Cl, 4-Cl Me CH N C—Cl H CF₃ 3-Cl, 4-Cl H NN CH H CF₃ 3-Cl, 4-Cl H N N N H CF₃ 3-Cl, 4-Cl H N N C—Cl H CF₃ 3-Cl,4-Cl Me N N CH H CF₃ 3-Cl, 4-Cl Me N N N H CF₃ 3-Cl, 4-Cl Me N N C—Cl HCF₃ 3-Cl, 5-Cl H CH N CH H CF₃ 3-Cl, 5-Cl H CH N N H CF₃ 3-Cl, 5-Cl H CHN C—Cl H CF₃ 3-Cl, 5-Cl Me CH N CH H CF₃ 3-Cl, 5-Cl Me CH N N H CF₃3-Cl, 5-Cl Me CH N C—Cl H CF₃ 3-Cl, 5-Cl H N N CH H CF₃ 3-Cl, 5-Cl H N NN H CF₃ 3-Cl, 5-Cl H N N C—Cl H CF₃ 3-Cl, 5-Cl Me N N CH H CF₃ 3-Cl,5-Cl Me N N N H CF₃ 3-Cl, 5-Cl Me N N C—Cl H CF₃ 3-Cl, 4-Cl H CH N CH ClCF₃ 3-Cl, 4-Cl H CH N N Cl CF₃ 3-Cl, 4-Cl H CH N C—Cl Cl CF₃ 3-Cl, 4-ClMe CH N CH Cl CF₃ 3-Cl, 4-Cl Me CH N N Cl CF₃ 3-Cl, 4-Cl Me CH N C—Cl ClCF₃ 3-Cl, 4-Cl H N N CH Cl CF₃ 3-Cl, 4-Cl H N N N Cl CF₃ 3-Cl, 4-Cl H NN C—Cl Cl CF₃ 3-Cl, 4-Cl Me N N CH Cl CF₃ 3-Cl, 4-Cl Me N N N Cl CF₃3-Cl, 4-Cl Me N N C—Cl Cl CF₃ 3-Cl, 5-Cl H CH N CH Cl CF₃ 3-Cl, 5-Cl HCH N N Cl CF₃ 3-Cl, 5-Cl H CH N C—Cl Cl CF₃ 3-Cl, 5-Cl Me CH N CH Cl CF₃3-Cl, 5-Cl Me CH N N Cl CF₃ 3-Cl, 5-Cl Me CH N C—Cl Cl CF₃ 3-Cl, 5-Cl HN N CH Cl CF₃ 3-Cl, 5-Cl H N N N Cl CF₃ 3-Cl, 5-Cl H N N C—Cl Cl CF₃3-Cl, 5-Cl Me N N CH Cl CF₃ 3-Cl, 5-Cl Me N N N Cl CF₃ 3-Cl, 5-Cl Me N NC—Cl Cl CF₃ 3-Cl, 4-Cl H CH N CH CF₃ CF₃ 3-Cl, 4-Cl H CH N N CF₃ CF₃3-Cl, 4-Cl H CH N C—Cl CF₃ CF₃ 3-Cl, 4-Cl Me CH N CH CF₃ CF₃ 3-Cl, 4-ClMe CH N N CF₃ CF₃ 3-Cl, 4-Cl Me CH N C—Cl CF₃ CF₃ 3-Cl, 4-Cl H N N CHCF₃ CF₃ 3-Cl, 4-Cl H N N N CF₃ CF₃ 3-Cl, 4-Cl H N N C—Cl CF₃ CF₃ 3-Cl,4-Cl Me N N CH CF₃ CF₃ 3-Cl, 4-Cl Me N N N CF₃ CF₃ 3-Cl, 4-Cl Me N NC—Cl CF₃ CF₃ 3-Cl, 5-Cl H CH N CH CF₃ CF₃ 3-Cl, 5-Cl H CH N N CF₃ CF₃3-Cl, 5-Cl H CH N C—Cl CF₃ CF₃ 3-Cl, 5-Cl Me CH N CH CF₃ CF₃ 3-Cl, 5-ClMe CH N N CF₃ CF₃ 3-Cl, 5-Cl Me CH N C—Cl CF₃ CF₃ 3-Cl, 5-Cl H N N CHCF₃ CF₃ 3-Cl, 5-Cl H N N N CF₃ CF₃ 3-Cl, 5-Cl H N N C—Cl CF₃ CF₃ 3-Cl,5-Cl Me N N CH CF₃ CF₃ 3-Cl, 5-Cl Me N N N CF₃ CF₃ 3-Cl, 5-Cl Me N NC—Cl CF₃

TABLE 11

B¹ B² B³ R³ A3 C—Cl CH CH Me CH C—Cl CH C—Cl Me CH C—Br CH CH Me CH C—BrCH C—Br Me CH C—Cl CH CH Me N C—Cl CH C—Cl Me N C—Br CH CH Me N C—Br CHC—Br Me N C—Cl CH CH F CH C—Cl CH C—Cl F CH C—Br CH CH F CH C—Br CH C—BrF CH C—Cl CH CH F N C—Cl CH C—Cl F N C—Br CH CH F N C—Br CH C—Br F NC—Cl CH CH Cl CH C—Cl CH C—Cl Cl CH C—Br CH CH Cl CH C—Br CH C—Br Cl CHC—Cl CH CH Cl N C—Cl CH C—Cl Cl N C—Br CH CH Cl N C—Br CH C—Br Cl N C—ClCH CH Br CH C—Cl CH C—Cl Br CH C—Br CH CH Br CH C—Br CH C—Br Br CH C—ClCH CH Br N C—Cl CH C—Cl Br N C—Br CH CH Br N C—Br CH C—Br Br N C—Cl CHCH I CH C—Cl CH C—Cl I CH C—Br CH CH I CH C—Br CH C—Br I CH C—Cl CH CH IN C—Cl CH C—Cl I N C—Br CH CH I N C—Br CH C—Br I N C—Cl CH CH —CN CHC—Cl CH C—Cl —CN CH C—Br CH CH —CN CH C—Br CH C—Br —CN CH C—Cl CH CH —CNN C—Cl CH C—Cl —CN N C—Br CH CH —CN N C—Br CH C—Br —CN N C—Cl CH CH CF₃CH C—Cl CH C—Cl CF₃ CH C—Br CH CH CF₃ CH C—Br CH C—Br CF₃ CH C—Cl CH CHCF₃ N C—Cl CH C—Cl CF₃ N C—Br CH CH CF₃ N C—Br CH C—Br CF₃ N C—Cl CH CHOCF₃ CH C—Cl CH C—Cl OCF₃ CH C—Br CH CH OCF₃ CH C—Br CH C—Br OCF₃ CHC—Cl CH CH OCF₃ N C—Cl CH C—Cl OCF₃ N C—Br CH CH OCF₃ N C—Br CH C—BrOCF₃ N C—Cl CH CH OMe CH C—Cl CH C—Cl OMe CH C—Br CH CH OMe CH C—Br CHC—Br OMe CH C—Cl CH CH OMe N C—Cl CH C—Cl OMe N C—Br CH CH OMe N C—Br CHC—Br OMe N C—Cl N CH Me CH C—Cl N C—Cl Me CH C—Br N CH Me CH C—Br N C—BrMe CH C—Cl N CH F CH C—Cl N C—Cl F CH C—Br N CH F CH C—Br N C—Br F CHC—Cl N CH Cl CH C—Cl N C—Cl Cl CH C—Br N CH Cl CH C—Br N C—Br Cl CH C—ClN CH Br CH C—Cl N C—Cl Br CH C—Br N CH Br CH C—Br N C—Br Br CH C—Cl N CHI CH C—Cl N C—Cl I CH C—Br N CH I CH C—Br N C—Br I CH C—Cl N CH —CN CHC—Cl N C—Cl —CN CH C—Br N CH —CN CH C—Br N C—Br —CN CH C—Cl N CH CF₃ CHC—Cl N C—Cl CF₃ CH C—Br N CH CF₃ CH C—Br N C—Br CF₃ CH C—Cl N CH OCF₃ CHC—Cl N C—Cl OCF₃ CH C—Br N CH OCF₃ CH C—Br N C—Br OCF₃ CH C—Cl N CH OMeCH C—Cl N C—Cl OMe CH C—Br N CH OMe CH C—Br N C—Br OMe CH C—Cl C—Cl CHMe CH C—Cl C—Cl C—Cl Me CH C—Br C—Cl CH Me CH C—Br C—Cl C—Br Me CH C—ClC—Cl CH Me N C—Cl C—Cl C—Cl Me N C—Br C—Cl CH Me N C—Br C—Cl C—Br Me NC—Cl C—Cl CH F CH C—Cl C—Cl C—Cl F CH C—Br C—Cl CH F CH C—Br C—Cl C—Br FCH C—Cl C—Cl CH F N C—Cl C—Cl C—Cl F N C—Br C—Cl CH F N C—Br C—Cl C—Br FN C—Cl C—Cl CH Cl CH C—Cl C—Cl C—Cl Cl CH C—Br C—Cl CH Cl CH C—Br C—ClC—Br Cl CH C—Cl C—Cl CH Cl N C—Cl C—Cl C—Cl Cl N C—Br C—Cl CH Cl N C—BrC—Cl C—Br Cl N C—Cl C—Cl CH Br CH C—Cl C—Cl C—Cl Br CH C—Br C—Cl CH BrCH C—Br C—Cl C—Br Br CH C—Cl C—Cl CH Br N C—Cl C—Cl C—Cl Br N C—Br C—ClCH Br N C—Br C—Cl C—Br Br N C—Cl C—Cl CH I CH C—Cl C—Cl C—Cl I CH C—BrC—Cl CH I CH C—Br C—Cl C—Br I CH C—Cl C—Cl CH I N C—Cl C—Cl C—Cl I NC—Br C—Cl CH I N C—Br C—Cl C—Br I N C—Cl C—Cl CH —CN CH C—Cl C—Cl C—Cl—CN CH C—Br C—Cl CH —CN CH C—Br C—Cl C—Br —CN CH C—Cl C—Cl CH —CN N C—ClC—Cl C—Cl —CN N C—Br C—Cl CH —CN N C—Br C—Cl C—Br —CN N C—Cl C—Cl CH CF₃CH C—Cl C—Cl C—Cl CF₃ CH C—Br C—Cl CH CF₃ CH C—Br C—Cl C—Br CF₃ CH C—ClC—Cl CH CF₃ N C—Cl C—Cl C—Cl CF₃ N C—Br C—Cl CH CF₃ N C—Br C—Cl C—Br CF₃N C—Cl C—Cl CH OCF₃ CH C—Cl C—Cl C—Cl OCF₃ CH C—Br C—Cl CH OCF₃ CH C—BrC—Cl C—Br OCF₃ CH C—Cl C—Cl CH OCF₃ N C—Cl C—Cl C—Cl OCF₃ N C—Br C—Cl CHOCF₃ N C—Br C—Cl C—Br OCF₃ N C—Cl C—Cl CH OMe CH C—Cl C—Cl C—Cl OMe CHC—Br C—Cl CH OMe CH C—Br C—Cl C—Br OMe CH C—Cl C—Cl CH OMe N C—Cl C—ClC—Cl OMe N C—Br C—Cl CH OMe N C—Br C—Cl C—Br OMe N C—Cl N CH Me N C—Cl NC—Cl Me N C—Br N CH Me N C—Br N C—Br Me N C—Cl N CH F N C—Cl N C—Cl F NC—Br N CH F N C—Br N C—Br F N C—Cl N CH Cl N C—Cl N C—Cl Cl N C—Br N CHCl N C—Br N C—Br Cl N C—Cl N CH Br N C—Cl N C—Cl Br N C—Br N CH Br NC—Br N C—Br Br N C—Cl N CH I N C—Cl N C—Cl I N C—Br N CH I N C—Br N C—BrI N C—Cl N CH —CN N C—Cl N C—Cl —CN N C—Br N CH —CN N C—Br N C—Br —CN NC—Cl N CH CF₃ N C—Cl N C—Cl CF₃ N C—Br N CH CF₃ N C—Br N C—Br CF₃ N C—ClN CH OCF₃ N C—Cl N C—Cl OCF₃ N C—Br N CH OCF₃ N C—Br N C—Br OCF₃ N C—ClN CH OMe N C—Cl N C—Cl OMe N C—Br N CH OMe N C—Br N C—Br OMe N

TABLE 12

(R²)_(k) R³ A³ p R²⁵ 3-Cl, 4-Cl H CH 0 Me 3-Cl, 4-Cl H CH 0 CH₂F 3-Cl,4-Cl H CH 0 CHF₂ 3-Cl, 4-Cl H CH 0 Et 3-Cl, 4-Cl H CH 0 CH₂CF₃ 3-Cl,4-Cl H CH 0 CH₂CN 3-Cl, 4-Cl H CH 0 n-Pr 3-Cl, 4-Cl H CH 0 i-Pr 3-Cl,4-Cl H CH 0 CH₂(2-Py) 3-Cl, 4-Cl H CH 0 c-Pr 3-Cl, 4-Cl H CH 0 CH₂(c-Pr)3-Cl, 4-Cl H CH 0 CH₂C═CH₂ 3-Cl, 4-Cl H CH 0 CH₂C≡CH 3-Cl, 4-Cl Me CH 0Me 3-Cl, 4-Cl Me CH 0 CH₂F 3-Cl, 4-Cl Me CH 0 CHF₂ 3-Cl, 4-Cl Me CH 0 Et3-Cl, 4-Cl Me CH 0 CH₂CF₃ 3-Cl, 4-Cl Me CH 0 CH₂CN 3-Cl, 4-Cl Me CH 0n-Pr 3-Cl, 4-Cl Me CH 0 i-Pr 3-Cl, 4-Cl Me CH 0 CH₂(2-Py) 3-Cl, 4-Cl MeCH 0 c-Pr 3-Cl, 4-Cl Me CH 0 CH₂(c-Pr) 3-Cl, 4-Cl Me CH 0 CH₂C═CH₂ 3-Cl,4-Cl Me CH 0 CH₂C≡CH 3-Cl, 4-Cl Cl CH 0 Me 3-Cl, 4-Cl Cl CH 0 CH₂F 3-Cl,4-Cl Cl CH 0 CHF₂ 3-Cl, 4-Cl Cl CH 0 Et 3-Cl, 4-Cl Cl CH 0 CH₂CF₃ 3-Cl,4-Cl Cl CH 0 CH₂CN 3-Cl, 4-Cl Cl CH 0 n-Pr 3-Cl, 4-Cl Cl CH 0 i-Pr 3-Cl,4-Cl Cl CH 0 CH₂(2-Py) 3-Cl, 4-Cl Cl CH 0 c-Pr 3-Cl, 4-Cl Cl CH 0CH₂(c-Pr) 3-Cl, 4-Cl Cl CH 0 CH₂C═CH₂ 3-Cl, 4-Cl Cl CH 0 CH₂C≡CH 3-Cl,5-Cl H CH 1 Me 3-Cl, 5-Cl H CH 1 CH₂F 3-Cl, 5-Cl H CH 1 CHF₂ 3-Cl, 5-ClH CH 1 Et 3-Cl, 5-Cl H CH 1 CH₂CF₃ 3-Cl, 5-Cl H CH 1 CH₂CN 3-Cl, 5-Cl HCH 1 n-Pr 3-Cl, 5-Cl H CH 1 i-Pr 3-Cl, 5-Cl H CH 1 CH₂(2-Py) 3-Cl, 5-ClH CH 1 c-Pr 3-Cl, 5-Cl H CH 1 CH₂(c-Pr) 3-Cl, 5-Cl H CH 1 CH₂C═CH₂ 3-Cl,5-Cl H CH 1 CH₂C≡CH 3-Cl, 5-Cl Me CH 1 Me 3-Cl, 5-Cl Me CH 1 CH₂F 3-Cl,5-Cl Me CH 1 CHF₂ 3-Cl, 5-Cl Me CH 1 Et 3-Cl, 5-Cl Me CH 1 CH₂CF₃ 3-Cl,5-Cl Me CH 1 CH₂CN 3-Cl, 5-Cl Me CH 1 n-Pr 3-Cl, 5-Cl Me CH 1 i-Pr 3-Cl,5-Cl Me CH 1 CH₂(2-Py) 3-Cl, 5-Cl Me CH 1 c-Pr 3-Cl, 5-Cl Me CH 1CH₂(c-Pr) 3-Cl, 5-Cl Me CH 1 CH₂C═CH₂ 3-Cl, 5-Cl Me CH 1 CH₂C≡CH 3-Cl,5-Cl Cl CH 1 Me 3-Cl, 5-Cl Cl CH 1 CH₂F 3-Cl, 5-Cl Cl CH 1 CHF₂ 3-Cl,5-Cl Cl CH 1 Et 3-Cl, 5-Cl Cl CH 1 CH₂CF₃ 3-Cl, 5-Cl Cl CH 1 CH₂CN 3-Cl,5-Cl Cl CH 1 n-Pr 3-Cl, 5-Cl Cl CH 1 i-Pr 3-Cl, 5-Cl Cl CH 1 CH₂(2-Py)3-Cl, 5-Cl Cl CH 1 c-Pr 3-Cl, 5-Cl Cl CH 1 CH₂(c-Pr) 3-Cl, 5-Cl Cl CH 1CH₂C═CH₂ 3-Cl, 5-Cl Cl CH 1 CH₂C≡CH 3-Cl, 5-Cl OMe CH 0 Me 3-Cl, 5-ClOMe CH 0 CH₂F 3-Cl, 5-Cl OMe CH 0 CHF₂ 3-Cl, 5-Cl OMe CH 0 Et 3-Cl, 5-ClOMe CH 0 CH₂CF₃ 3-Cl, 5-Cl OMe CH 0 CH₂CN 3-Cl, 5-Cl OMe CH 0 n-Pr 3-Cl,5-Cl OMe CH 0 i-Pr 3-Cl, 5-Cl OMe CH 0 CH₂(2-Py) 3-Cl, 5-Cl OMe CH 0c-Pr 3-Cl, 5-Cl OMe CH 0 CH₂(c-Pr) 3-Cl, 5-Cl OMe CH 0 CH₂C═CH₂ 3-Cl,5-Cl OMe CH 0 CH₂C≡CH 3-Cl, 5-Cl OMe CH 1 Me 3-Cl, 5-Cl OMe CH 1 CH₂F3-Cl, 5-Cl OMe CH 1 CHF₂ 3-Cl, 5-Cl OMe CH 1 Et 3-Cl, 5-Cl OMe CH 1CH₂CF₃ 3-Cl, 5-Cl OMe CH 1 CH₂CN 3-Cl, 5-Cl OMe CH 1 n-Pr 3-Cl, 5-Cl OMeCH 1 i-Pr 3-Cl, 5-Cl OMe CH 1 CH₂(2-Py) 3-Cl, 5-Cl OMe CH 1 c-Pr 3-Cl,5-Cl OMe CH 1 CH₂(c-Pr) 3-Cl, 5-Cl OMe CH 1 CH₂C═CH₂ 3-Cl, 5-Cl OMe CH 1CH₂C≡CH 3-Cl, 5-Cl OMe CH 2 Me 3-Cl, 5-Cl OMe CH 2 CH₂F 3-Cl, 5-Cl OMeCH 2 CHF₂ 3-Cl, 5-Cl OMe CH 2 Et 3-Cl, 5-Cl OMe CH 2 CH₂CF₃ 3-Cl, 5-ClOMe CH 2 CH₂CN 3-Cl, 5-Cl OMe CH 2 n-Pr 3-Cl, 5-Cl OMe CH 2 i-Pr 3-Cl,5-Cl OMe CH 2 CH₂(2-Py) 3-Cl, 5-Cl OMe CH 2 c-Pr 3-Cl, 5-Cl OMe CH 2CH₂(c-Pr) 3-Cl, 5-Cl OMe CH 2 CH₂C═CH₂ 3-Cl, 5-Cl OMe CH 2 CH₂C≡CH 3-Cl,5-Cl CN CH 0 Me 3-Cl, 5-Cl CN CH 0 CH₂F 3-Cl, 5-Cl CN CH 0 CHF₂ 3-Cl,5-Cl CN CH 0 Et 3-Cl, 5-Cl CN CH 0 CH₂CF₃ 3-Cl, 5-Cl CN CH 0 CH₂CN 3-Cl,5-Cl CN CH 0 n-Pr 3-Cl, 5-Cl CN CH 0 i-Pr 3-Cl, 5-Cl CN CH 0 CH₂(2-Py)3-Cl, 5-Cl CN CH 0 c-Pr 3-Cl, 5-Cl CN CH 0 CH₂(c-Pr) 3-Cl, 5-Cl CN CH 0CH₂C═CH₂ 3-Cl, 5-Cl CN CH 0 CH₂C≡CH 3-Cl, 5-Cl CN CH 2 Me 3-Cl, 5-Cl CNCH 2 CH₂F 3-Cl, 5-Cl CN CH 2 CHF₂ 3-Cl, 5-Cl CN CH 2 Et 3-Cl, 5-Cl CN CH2 CH₂CF₃ 3-Cl, 5-Cl CN CH 2 CH₂CN 3-Cl, 5-Cl CN CH 2 n-Pr 3-Cl, 5-Cl H N0 Me 3-Cl, 5-Cl H N 0 Et 3-Cl, 5-Cl H N 0 CH₂CF₃ 3-Cl, 5-Cl H N 0 CH₂CN3-Cl, 5-Cl H N 0 n-Pr 3-Cl, 5-Cl H N 0 i-Pr 3-Cl, 5-Cl H N 0 CH₂(2-Py)3-Cl, 5-Cl Me N 0 Me 3-Cl, 5-Cl Me N 0 Et 3-Cl, 5-Cl Me N 0 CH₂CF₃ 3-Cl,5-Cl Me N 0 CH₂CN 3-Cl, 5-Cl Me N 0 n-Pr 3-Cl, 5-Cl Me N 0 i-Pr 3-Cl,5-Cl Me N 0 CH₂(2-Py) 3-Cl, 5-Cl CF₃ N 0 Me 3-Cl, 5-Cl CF₃ N 0 Et 3-Cl,5-Cl CF₃ N 0 CH₂CF₃ 3-Cl, 5-Cl CF₃ N 0 CH₂CN 3-Cl, 5-Cl CF₃ N 0 n-Pr3-Cl, 5-Cl CF₃ N 0 i-Pr 3-Cl, 5-Cl CF₃ N 0 CH₂(2-Py) 3-Cl, 5-Cl H CH 0Me 3-Cl, 5-Cl H CH 0 CH₂F 3-Cl, 5-Cl H CH 0 CHF₂ 3-Cl, 5-Cl H CH 0 Et3-Cl, 5-Cl H CH 0 CH₂CF₃ 3-Cl, 5-Cl H CH 0 CH₂CN 3-Cl, 5-Cl H CH 0 n-Pr3-Cl, 5-Cl H CH 0 i-Pr 3-Cl, 5-Cl H CH 0 CH₂(2-Py) 3-Cl, 5-Cl H CH 0c-Pr 3-Cl, 5-Cl H CH 0 CH₂(c-Pr) 3-Cl, 5-Cl H CH 0 CH₂C═CH₂ 3-Cl, 5-Cl HCH 0 CH₂C≡CH 3-Cl, 5-Cl Me CH 0 Me 3-Cl, 5-Cl Me CH 0 CH₂F 3-Cl, 5-Cl MeCH 0 CHF₂ 3-Cl, 5-Cl Me CH 0 Et 3-Cl, 5-Cl Me CH 0 CH₂CF₃ 3-Cl, 5-Cl MeCH 0 CH₂CN 3-Cl, 5-Cl Me CH 0 n-Pr 3-Cl, 5-Cl Me CH 0 i-Pr 3-Cl, 5-Cl MeCH 0 CH₂(2-Py) 3-Cl, 5-Cl Me CH 0 c-Pr 3-Cl, 5-Cl Me CH 0 CH₂(c-Pr)3-Cl, 5-Cl Me CH 0 CH₂C═CH₂ 3-Cl, 5-Cl Me CH 0 CH₂C≡CH 3-Cl, 5-Cl Cl CH0 Me 3-Cl, 5-Cl Cl CH 0 CH₂F 3-Cl, 5-Cl Cl CH 0 CHF₂ 3-Cl, 5-Cl Cl CH 0Et 3-Cl, 5-Cl Cl CH 0 CH₂CF₃ 3-Cl, 5-Cl Cl CH 0 CH₂CN 3-Cl, 5-Cl Cl CH 0n-Pr 3-Cl, 5-Cl Cl CH 0 i-Pr 3-Cl, 5-Cl Cl CH 0 CH₂(2-Py) 3-Cl, 5-Cl ClCH 0 c-Pr 3-Cl, 5-Cl Cl CH 0 CH₂(c-Pr) 3-Cl, 5-Cl Cl CH 0 CH₂C═CH₂ 3-Cl,5-Cl Cl CH 0 CH₂C≡CH 3-Cl, 5-Cl H CH 2 Me 3-Cl, 5-Cl H CH 2 CH₂F 3-Cl,5-Cl H CH 2 CHF₂ 3-Cl, 5-Cl H CH 2 Et 3-Cl, 5-Cl H CH 2 CH₂CF₃ 3-Cl,5-Cl H CH 2 CH₂CN 3-Cl, 5-Cl H CH 2 n-Pr 3-Cl, 5-Cl H CH 2 i-Pr 3-Cl,5-Cl H CH 2 CH₂(2-Py) 3-Cl, 5-Cl H CH 2 c-Pr 3-Cl, 5-Cl H CH 2 CH₂(c-Pr)3-Cl, 5-Cl H CH 2 CH₂C═CH₂ 3-Cl, 5-Cl H CH 2 CH₂C≡CH 3-Cl, 5-Cl Me CH 2Me 3-Cl, 5-Cl Me CH 2 CH₂F 3-Cl, 5-Cl Me CH 2 CHF₂ 3-Cl, 5-Cl Me CH 2 Et3-Cl, 5-Cl Me CH 2 CH₂CF₃ 3-Cl, 5-Cl Me CH 2 CH₂CN 3-Cl, 5-Cl Me CH 2n-Pr 3-Cl, 5-Cl Me CH 2 i-Pr 3-Cl, 5-Cl Me CH 2 CH₂(2-Py) 3-Cl, 5-Cl MeCH 2 c-Pr 3-Cl, 5-Cl Me CH 2 CH₂(c-Pr) 3-Cl, 5-Cl Me CH 2 CH₂C═CH₂ 3-Cl,5-Cl Me CH 2 CH₂C≡CH 3-Cl, 5-Cl Cl CH 2 Me 3-Cl, 5-Cl Cl CH 2 CH₂F 3-Cl,5-Cl Cl CH 2 CHF₂ 3-Cl, 5-Cl Cl CH 2 Et 3-Cl, 5-Cl Cl CH 2 CH₂CF₃ 3-Cl,5-Cl Cl CH 2 CH₂CN 3-Cl, 5-Cl Cl CH 2 n-Pr 3-Cl, 5-Cl Cl CH 2 i-Pr 3-Cl,5-Cl Cl CH 2 CH₂(2-Py) 3-Cl, 5-Cl Cl CH 2 c-Pr 3-Cl, 5-Cl Cl CH 2CH₂(c-Pr) 3-Cl, 5-Cl Cl CH 2 CH₂C═CH₂ 3-Cl, 5-Cl Cl CH 2 CH₂C≡CH 3-Cl,5-Cl CF₃ CH 0 Me 3-Cl, 5-Cl CF₃ CH 0 CH₂F 3-Cl, 5-Cl CF₃ CH 0 CHF₂ 3-Cl,5-Cl CF₃ CH 0 Et 3-Cl, 5-Cl CF₃ CH 0 CH₂CF₃ 3-Cl, 5-Cl CF₃ CH 0 CH₂CN3-Cl, 5-Cl CF₃ CH 0 n-Pr 3-Cl, 5-Cl CF₃ CH 0 i-Pr 3-Cl, 5-Cl CF₃ CH 0CH₂(2-Py) 3-Cl, 5-Cl CF₃ CH 0 c-Pr 3-Cl, 5-Cl CF₃ CH 0 CH₂(c-Pr) 3-Cl,5-Cl CF₃ CH 0 CH₂C═CH₂ 3-Cl, 5-Cl CF₃ CH 0 CH₂C≡CH 3-Cl, 5-Cl CF₃ CH 1Me 3-Cl, 5-Cl CF₃ CH 1 CH₂F 3-Cl, 5-Cl CF₃ CH 1 CHF₂ 3-Cl, 5-Cl CF₃ CH 1Et 3-Cl, 5-Cl CF₃ CH 1 CH₂CF₃ 3-Cl, 5-Cl CF₃ CH 1 CH₂CN 3-Cl, 5-Cl CF₃CH 1 n-Pr 3-Cl, 5-Cl CF₃ CH 1 i-Pr 3-Cl, 5-Cl CF₃ CH 1 CH₂(2-Py) 3-Cl,5-Cl CF₃ CH 1 c-Pr 3-Cl, 5-Cl CF₃ CH 1 CH₂(c-Pr) 3-Cl, 5-Cl CF₃ CH 1CH₂C═CH₂ 3-Cl, 5-Cl CF₃ CH 1 CH₂C≡CH 3-Cl, 5-Cl CF₃ CH 2 Me 3-Cl, 5-ClCF₃ CH 2 CH₂F 3-Cl, 5-Cl CF₃ CH 2 CHF₂ 3-Cl, 5-Cl CF₃ CH 2 Et 3-Cl, 5-ClCF₃ CH 2 CH₂CF₃ 3-Cl, 5-Cl CF₃ CH 2 CH₂CN 3-Cl, 5-Cl CF₃ CH 2 n-Pr 3-Cl,5-Cl CF₃ CH 2 i-Pr 3-Cl, 5-Cl CF₃ CH 2 CH₂(2-Py) 3-Cl, 5-Cl CF₃ CH 2c-Pr 3-Cl, 5-Cl CF₃ CH 2 CH₂(c-Pr) 3-Cl, 5-Cl CF₃ CH 2 CH₂C═CH₂ 3-Cl,5-Cl CF₃ CH 2 CH₂C≡CH 3-Cl, 5-Cl CN CH 1 Me 3-Cl, 5-Cl CN CH 1 CH₂F3-Cl, 5-Cl CN CH 1 CHF₂ 3-Cl, 5-Cl CN CH 1 Et 3-Cl, 5-Cl CN CH 1 CH₂CF₃3-Cl, 5-Cl CN CH 1 CH₂CN 3-Cl, 5-Cl CN CH 1 n-Pr 3-Cl, 5-Cl CN CH 1 i-Pr3-Cl, 5-Cl CN CH 1 CH₂(2-Py) 3-Cl, 5-Cl CN CH 1 c-Pr 3-Cl, 5-Cl CN CH 1CH₂(c-Pr) 3-Cl, 5-Cl CN CH 1 CH₂C═CH₂ 3-Cl, 5-Cl CN CH 1 CH₂C≡CH 3-Cl,5-Cl CN CH 2 i-Pr 3-Cl, 5-Cl CN CH 2 CH₂(2-Py) 3-Cl, 5-Cl CN CH 2 c-Pr3-Cl, 5-Cl CN CH 2 CH₂(c-Pr) 3-Cl, 5-Cl CN CH 2 CH₂C═CH₂ 3-Cl, 5-Cl CNCH 2 CH₂C≡CH 3-Cl, 5-Cl Cl N 0 Me 3-Cl, 5-Cl Cl N 0 Et 3-Cl, 5-Cl Cl N 0CH₂CF₃ 3-Cl, 5-Cl Cl N 0 CH₂CN 3-Cl, 5-Cl Cl N 0 n-Pr 3-Cl, 5-Cl Cl N 0i-Pr 3-Cl, 5-Cl Cl N 0 CH₂(2-Py) 3-Cl, 5-Cl OMe N 0 Me 3-Cl, 5-Cl OMe N0 Et 3-Cl, 5-Cl OMe N 0 CH₂CF₃ 3-Cl, 5-Cl OMe N 0 CH₂CN 3-Cl, 5-Cl OMe N0 n-Pr 3-Cl, 5-Cl OMe N 0 i-Pr 3-Cl, 5-Cl OMe N 0 CH₂(2-Py) 3-Cl, 5-ClCN N 0 Me 3-Cl, 5-Cl CN N 0 Et 3-Cl, 5-Cl CN N 0 CH₂CF₃ 3-Cl, 5-Cl CN N0 CH₂CN 3-Cl, 5-Cl CN N 0 n-Pr 3-Cl, 5-Cl CN N 0 i-Pr 3-Cl, 5-Cl CN N 0CH₂(2-Py)

TABLE 13

(R²)_(k) R³ A³ R²⁸ R²⁹ 3-Cl, 5-Cl H CH H Me 3-Cl, 5-Cl H CH H Et 3-Cl,5-Cl H CH H CH₂CF₃ 3-Cl, 5-Cl H CH H i-Pr 3-Cl, 5-Cl H CH H c-Pr 3-Cl,5-Cl Cl CH H Me 3-Cl, 5-Cl Cl CH H Et 3-Cl, 5-Cl Cl CH H CH₂CF₃ 3-Cl,5-Cl Cl CH H i-Pr 3-Cl, 5-Cl Cl CH H c-Pr 3-Cl, 5-Cl Me CH H Me 3-Cl,5-Cl Me CH H Et 3-Cl, 5-Cl Me CH H CH₂CF₃ 3-Cl, 5-Cl Me CH H i-Pr 3-Cl,5-Cl Me CH H c-Pr 3-Cl, 5-Cl CN CH H Me 3-Cl, 5-Cl CN CH H Et 3-Cl, 5-ClCN CH H CH₂CF₃ 3-Cl, 5-Cl CN CH H i-Pr 3-Cl, 5-Cl CN CH H c-Pr 3-Cl,5-Cl H CH CN Me 3-Cl, 5-Cl H CH CN Et 3-Cl, 5-Cl H CH CN CH₂CF₃ 3-Cl,5-Cl H CH CN i-Pr 3-Cl, 5-Cl H CH CN c-Pr 3-Cl, 5-Cl Cl CH CN Me 3-Cl,5-Cl Cl CH CN Et 3-Cl, 5-Cl Cl CH CN CH₂CF₃ 3-Cl, 5-Cl Cl CH CN i-Pr3-Cl, 5-Cl Cl CH CN c-Pr 3-Cl, 5-Cl Me CH CN Me 3-Cl, 5-Cl Me CH CN Et3-Cl, 5-Cl Me CH CN CH₂CF₃ 3-Cl, 5-Cl Me CH CN i-Pr 3-Cl, 5-Cl Me CH CNc-Pr 3-Cl, 5-Cl CN CH CN Me 3-Cl, 5-Cl CN CH CN Et 3-Cl, 5-Cl CN CH CNCH₂CF₃ 3-Cl, 5-Cl CN CH CN i-Pr 3-Cl, 5-Cl CN CH CN c-Pr 3-Cl, 5-Cl H NH Me 3-Cl, 5-Cl H N H Et 3-Cl, 5-Cl H N H CH₂CF₃ 3-Cl, 5-Cl H N H i-Pr3-Cl, 5-Cl H N H c-Pr 3-Cl, 5-Cl H N CN Me 3-Cl, 5-Cl H N CN Et 3-Cl,5-Cl H N CN CH₂CF₃ 3-Cl, 5-Cl H N CN i-Pr 3-Cl, 5-Cl H N CN c-Pr 3-Cl,5-Cl Cl N H Me 3-Cl, 5-Cl Cl N H Et 3-Cl, 5-Cl Cl N H CH₂CF₃ 3-Cl, 5-ClCl N H i-Pr 3-Cl, 5-Cl Cl N H c-Pr 3-Cl, 5-Cl Cl N CN Me 3-Cl, 5-Cl Cl NCN Et 3-Cl, 5-Cl Cl N CN CH₂CF₃ 3-Cl, 5-Cl Cl N CN i-Pr 3-Cl, 5-Cl Cl NCN c-Pr 3-Cl, 5-Cl Me N H Me 3-Cl, 5-Cl Me N H Et 3-Cl, 5-Cl Me N HCH₂CF₃ 3-Cl, 5-Cl Me N H i-Pr 3-Cl, 5-Cl Me N H c-Pr 3-Cl, 5-Cl Me N CNMe 3-Cl, 5-Cl Me N CN Et 3-Cl, 5-Cl Me N CN CH₂CF₃ 3-Cl, 5-Cl Me N CNi-Pr 3-Cl, 5-Cl Me N CN c-Pr 3-Cl, 5-Cl CN N H Me 3-Cl, 5-Cl CN N H Et3-Cl, 5-Cl CN N H CH₂CF₃ 3-Cl, 5-Cl CN N H i-Pr 3-Cl, 5-Cl CN N H c-Pr3-Cl, 5-Cl CN N CN Me 3-Cl, 5-Cl CN N CN Et 3-Cl, 5-Cl CN N CN CH₂CF₃3-Cl, 5-Cl CN N CN i-Pr 3-Cl, 5-Cl CN N CN c-Pr 3-Cl, 5-Cl H CH COCF₃ Me3-Cl, 5-Cl H CH COCF₃ Et 3-Cl, 5-Cl H CH COCF₃ CH₂CF₃ 3-Cl, 5-Cl H CHCOCF₃ i-Pr 3-Cl, 5-Cl H CH COCF₃ c-Pr 3-Cl, 5-Cl Cl CH COCF₃ Me 3-Cl,5-Cl Cl CH COCF₃ Et 3-Cl, 5-Cl Cl CH COCF₃ CH₂CF₃ 3-Cl, 5-Cl Cl CH COCF₃i-Pr 3-Cl, 5-Cl Cl CH COCF₃ c-Pr 3-Cl, 5-Cl Me CH COCF₃ Me 3-Cl, 5-Cl MeCH COCF₃ Et 3-Cl, 5-Cl Me CH COCF₃ CH₂CF₃ 3-Cl, 5-Cl Me CH COCF₃ i-Pr3-Cl, 5-Cl Me CH COCF₃ c-Pr 3-Cl, 5-Cl CN CH COCF₃ Me 3-Cl, 5-Cl CN CHCOCF₃ Et 3-Cl, 5-Cl CN CH COCF₃ CH₂CF₃ 3-Cl, 5-Cl CN CH COCF₃ i-Pr 3-Cl,5-Cl CN CH COCF₃ c-Pr 3-Cl, 5-Cl H CH NO₂ Me 3-Cl, 5-Cl H CH NO₂ Et3-Cl, 5-Cl H CH NO₂ CH₂CF₃ 3-Cl, 5-Cl H CH NO₂ i-Pr 3-Cl, 5-Cl H CH NO₂c-Pr 3-Cl, 5-Cl Cl CH NO₂ Me 3-Cl, 5-Cl Cl CH NO₂ Et 3-Cl, 5-Cl Cl CHNO₂ CH₂CF₃ 3-Cl, 5-Cl Cl CH NO₂ i-Pr 3-Cl, 5-Cl Cl CH NO₂ c-Pr 3-Cl,5-Cl Me CH NO₂ Me 3-Cl, 5-Cl Me CH NO₂ Et 3-Cl, 5-Cl Me CH NO₂ CH₂CF₃3-Cl, 5-Cl Me CH NO₂ i-Pr 3-Cl, 5-Cl Me CH NO₂ c-Pr 3-Cl, 5-Cl CN CH NO₂Me 3-Cl, 5-Cl CN CH NO₂ Et 3-Cl, 5-Cl CN CH NO₂ CH₂CF₃ 3-Cl, 5-Cl CN CHNO₂ i-Pr 3-Cl, 5-Cl CN CH NO₂ c-Pr 3-Cl, 5-Cl H N COCF₃ Me 3-Cl, 5-Cl HN COCF₃ Et 3-Cl, 5-Cl H N COCF₃ CH₂CF₃ 3-Cl, 5-Cl H N COCF₃ i-Pr 3-Cl,5-Cl H N COCF₃ c-Pr 3-Cl, 5-Cl H N NO₂ Me 3-Cl, 5-Cl H N NO₂ Et 3-Cl,5-Cl H N NO₂ CH₂CF₃ 3-Cl, 5-Cl H N NO₂ i-Pr 3-Cl, 5-Cl H N NO₂ c-Pr3-Cl, 5-Cl Cl N COCF₃ Me 3-Cl, 5-Cl Cl N COCF₃ Et 3-Cl, 5-Cl Cl N COCF₃CH₂CF₃ 3-Cl, 5-Cl Cl N COCF₃ i-Pr 3-Cl, 5-Cl Cl N COCF₃ c-Pr 3-Cl, 5-ClCl N NO₂ Me 3-Cl, 5-Cl Cl N NO₂ Et 3-Cl, 5-Cl Cl N NO₂ CH₂CF₃ 3-Cl, 5-ClCl N NO₂ i-Pr 3-Cl, 5-Cl Cl N NO₂ c-Pr 3-Cl, 5-Cl Me N COCF₃ Me 3-Cl,5-Cl Me N COCF₃ Et 3-Cl, 5-Cl Me N COCF₃ CH₂CF₃ 3-Cl, 5-Cl Me N COCF₃i-Pr 3-Cl, 5-Cl Me N COCF₃ c-Pr 3-Cl, 5-Cl Me N NO₂ Me 3-Cl, 5-Cl Me NNO₂ Et 3-Cl, 5-Cl Me N NO₂ CH₂CF₃ 3-Cl, 5-Cl Me N NO₂ i-Pr 3-Cl, 5-Cl MeN NO₂ c-Pr 3-Cl, 5-Cl CN N COCF₃ Me 3-Cl, 5-Cl CN N COCF₃ Et 3-Cl, 5-ClCN N COCF₃ CH₂CF₃ 3-Cl, 5-Cl CN N COCF₃ i-Pr 3-Cl, 5-Cl CN N COCF₃ c-Pr3-Cl, 5-Cl CN N NO₂ Me 3-Cl, 5-Cl CN N NO₂ Et 3-Cl, 5-Cl CN N NO₂ CH₂CF₃3-Cl, 5-Cl CN N NO₂ i-Pr 3-Cl, 5-Cl CN N NO₂ c-Pr

Formulation/Utility

A compound of this invention will generally be used as an invertebratepest control active ingredient in a composition, i.e. formulation, withat least one additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents, which serves as acarrier. The formulation or composition ingredients are selected to beconsistent with the physical properties of the active ingredient, modeof application and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions and/or suspoemulsions)and the like, which optionally can be thickened into gels. The generaltypes of aqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsionand suspo-emulsion. The general types of nonaqueous liquid compositionsare emulsifiable concentrate, microemulsifiable concentrate, dispersibleconcentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength composition'sare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water. Spray volumes canrange from about from about one to several thousand liters per hectare,but more typically are in the range from about ten to several hundredliters per hectare. Sprayable formulations can be tank mixed with wateror another suitable medium for foliar treatment by aerial or groundapplication, or for application to the growing medium of the plant.Liquid and dry formulations can be metered directly into drip irrigationsystems or metered into the furrow during planting. Liquid and solidformulations can be applied onto seeds of crops and other desirablevegetation as seed treatments before planting to protect developingroots and other subterranean plant parts and/or foliage through systemicuptake.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol,triethylene glycol, propylene glycol, dipropylene glycol, polypropyleneglycol, propylene carbonate, butylene carbonate, paraffins (e.g., whitemineral oils, normal paraffins, isoparaffins), alkylbenzenes,alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, triacetin,aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes,alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone,isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamylacetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate,tridecyl acetate and isobornyl acetate, other esters such as alkylatedlactate esters, dibasic esters and γ-butyrolactone, and alcohols, whichcan be linear, branched, saturated or unsaturated. Such as methanol,ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol,n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol,isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleylalcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol andbenzyl alcohol. Liquid diluents also include glycerol esters ofsaturated and unsaturated fatty acids (typically C₆-C₂₂), such as plantseed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn(maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean,rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beeftallow, pork tallow, lard, cod liver oil, fish oil), and mixturesthereof. Liquid diluents also include alkylated fatty acids (e.g.,methylated, ethylated, butylated) wherein the fatty acids may beobtained by hydrolysis of glycerol esters from plant and animal sources,and can be purified by distillation. Typical liquid diluents aredescribed in Marsden, Solvents Guide, 2nd Ed., Interscience, New York,1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polyethers prepared from ethylene oxide or propyleneoxide and reverse block polymers where the terminal blocks are preparedfrom propylene oxide; ethoxylated fatty acids; ethoxylated fatty estersand oils; ethoxylated methyl esters; ethoxylated tristyrylphenol(including those prepared from ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof); fatty acid esters, glycerol esters,lanolin-based derivatives, polyethoxylate esters such as polyethoxylatedsorbitan fatty acid esters, polyethoxylated sorbitol fatty acid estersand polyethoxylated glycerol fatty acid esters, other sorbitanderivatives such as sorbitan esters; polymeric surfactants such asrandom copolymers, block copolymers, alkyd peg (polyethylene glycol)resins, graft or comb polymers and star polymers; polyethylene glycols(pegs); polyethylene glycol fatty acid esters; silicone-basedsurfactants; and sugar-derivatives such as sucrose esters, alkylpolyglycosides and alkyl polysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylene-tetramines, and ethoxylatedamines, ethoxylated diamines and propoxylated amines (prepared from theamines and ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-D. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be constructed as merely illustrative, andnot limiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate Compound 9 98.5% silica aerogel 0.5% syntheticamorphous fine silica 1.0%

Example B

Wettable Powder Compound 14 65.0% dodecylphenol polyethylene glycolether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example C

Granule Compound 26 10.0% attapulgite granules (low volatile matter,0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet Compound 38 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate Compound 42 10.0% polyoxyethylene sorbitolhexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion Compound 63 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water20.0%

Example G

Seed Treatment Compound 72 20.00% polyvinylpyrrolidone-vinyl acetatecopolymer 5.00% montan acid wax 5.00% calcium ligninsulfonate 1.00%polyoxyethylene/polyoxypropylene block copolymers 1.00% stearyl alcohol(POE 20) 2.00% polyorganosilane 0.20% colorant red dye 0.05% water65.75%

Example H

Fertilizer Stick Compound 107 2.5% pyrrolidone-styrene copolymer 4.8%tristyrylphenyl 16-ethoxylate 2.3% talc 0.8% corn starch 5.0%Nitrophoska ® Permanent 15-9-15 slow- 36.0% release fertilizer (BASF)kaolin 38.0% water 10.6%

Compounds of this invention exhibit activity against a wide spectrum ofinvertebrate pests. These pests include invertebrates inhabiting avariety of environments such as, for example, plant foliage, roots,soil, harvested crops or other foodstuffs, building structures or animalinteguments. These pests include, for example, invertebrates feeding onfoliage (including leaves, stems, flowers and fruits), seeds, wood,textile fibers or animal blood or tissues, and thereby causing injury ordamage to, for example, growing or stored agronomic crops, forests,greenhouse crops, ornamentals, nursery crops, stored foodstuffs or fiberproducts, or houses or other structures or their contents, or beingharmful to animal health or public health. Those skilled in the art willappreciate that not all compounds are equally effective against allgrowth stages of all pests.

These present compounds and compositions are thus useful agronomicallyfor protecting field crops from phytophagous invertebrate pests, andalso nonagronomically for protecting other horticultural crops andplants from phytophagous invertebrate pests. This utility includesprotecting crops and other plants (i.e. both agronomic and nonagronomic)that contain genetic material introduced by genetic engineering (i.e.transgenic) or modified by mutagenesis to provide advantageous traits.Examples of such traits include tolerance to herbicides, resistance tophytophagous pests (e.g., insects, mites, aphids, spiders, nematodes,snails, plant-pathogenic fungi, bacteria and viruses), improved plantgrowth, increased tolerance of adverse growing conditions such as highor low temperatures, low or high soil moisture, and high salinity,increased flowering or fruiting, greater harvest yields, more rapidmaturation, higher quality and/or nutritional value of the harvestedproduct, or improved storage or process properties of the harvestedproducts. Transgenic plants can be modified to express multiple traits.Examples of plants containing traits provided by genetic engineering ormutagenesis include varieties of corn, cotton, soybean and potatoexpressing an insecticidal Bacillus thuringiensis toxin such as YIELDGARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, andherbicide-tolerant varieties of corn, cotton, soybean and rapeseed suchas ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®, as well ascrops expressing N-acetyltransferase (GAT) to provide resistance toglyphosate herbicide, or crops containing the HRA gene providingresistance to herbicides inhibiting acetolactate synthase (ALS). Thepresent compounds and compositions may interact synergistically withtraits introduced by genetic engineering or modified by mutagenesis,thus enhancing phenotypic expression or effectiveness of the traits orincreasing the invertebrate pest control effectiveness of the presentcompounds and compositions. In particular, the present compounds andcompositions may interact synergistically with the phenotypic expressionof proteins or other natural products toxic to invertebrate pests toprovide greater-than-additive control of these pests.

Nonagronomic uses refer to invertebrate pest control in the areas otherthan fields of crop plants. Nonagronomic uses of the present compoundsand compositions include control of invertebrate pests in stored grains,beans and other foodstuffs, and in textiles such as clothing andcarpets. Nonagronomic uses of the present compounds and compositionsalso include invertebrate pest control in ornamental plants, forests, inyards, along roadsides and railroad rights of way, and on turf such aslawns, golf courses and pastures. Nonagronomic uses of the presentcompounds and compositions also include invertebrate pest control inhouses and other buildings which may be occupied by humans and/orcompanion, farm, ranch, zoo or other animals. Nonagronomic uses of thepresent compounds and compositions also include the control of pestssuch as termites that can damage wood or other structural materials usedin buildings.

Nonagronomic uses of the present compounds and compositions also includeprotecting human and animal health by controlling invertebrate peststhat are parasitic or transmit infectious diseases. The controlling ofanimal parasites includes controlling external parasites that areparasitic to the surface of the body of the host animal (e.g.,shoulders, armpits, abdomen, inner part of the thighs) and internalparasites that are parasitic to the inside of the body of the hostanimal (e.g., stomach, intestine, lung, veins, under the skin, lymphatictissue). External parasitic or disease transmitting pests include, forexample, chiggers, ticks, lice, mosquitoes, flies, mites and fleas.Internal parasites include heartworms, hookworms and helminths.Compounds and compositions of the present invention are suitable forsystemic and/or non-systemic control of infestation or infection byparasites on animals. Compounds and compositions of the presentinvention are particularly suitable for combating external parasitic ordisease transmitting pests. Compounds and compositions of the presentinvention are suitable for combating parasites that infest agriculturalworking animals, such as cattle, sheep, goats, horses, pigs, donkeys,camels, buffaloes, rabbits, hens, turkeys, ducks, geese and bees; petanimals and domestic animals such as dogs, cats, pet birds and aquariumfish; as well as so-called experimental animals, such as hamsters,guinea pigs, rats and mice. By combating these parasites, fatalities andperformance reduction (in terms of meat, milk, wool, skins, eggs, honey,etc.) are reduced, so that applying a composition comprising a compoundof the present invention allows more economic and simple husbandry ofanimals.

Examples of agronomic or nonagronomic invertebrate pests include eggs,larvae and adults of the order Lepidoptera, such as armyworms, cutworms,loopers, and heliothines in the family Noctuidae (e.g., pink stem borer(Sesamia inferens Walker), corn stalk borer (Sesamia nonagrioidesLefebvre), southern armyworm (Spodoptera eridania Cramer), fall armyworm(Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exiguaHübner), cotton leafworm (Spodoptera littoralis Boisduval),yellowstriped armyworm (Spodoptera ornithogalli Guenée), black cutworm(Agrotis ipsilon Hufnagel), velvetbean caterpillar (Anticarsiagemmatalis Hübner), green fruitworm (Lithophane antennata Walker),cabbage armyworm (Barathra brassicae Linnaeus), soybean looper(Pseudoplusia includens Walker), cabbage looper (Trichoplusia niHübner), tobacco budworm (Heliothis virescens Fabricius)); borers,casebearers, webworms, coneworms, cabbageworms and skeletonizers fromthe family Pyralidae (e.g., European corn borer (Ostrinia nubilalisHübner), navel orangeworm (Amyelois transitella Walker), corn rootwebworm (Crambus caliginosellus Clemens), sod webworms (Pyralidae:Crambinae) such as sod worm (Herpetogramma licarsisalis Walker),sugarcane stem borer (Chilo infuscatellus Snellen), tomato small borer(Neoleucinodes elegantalis Guenée), green leafroller (Cnaphalocerusmedinalis), grape leaffolder (Desmia funeralis Hübner), melon worm(Diaphania nitidalis Stoll), cabbage center grub (Helluala hydralisGuenée), yellow stem borer (Scirpophaga incertulas Walker), early shootborer (Scirpophaga infuscatellus Snellen), white stem borer (Scirpophagainnotata Walker), top shoot borer (Scirpophaga nivella Fabricius),dark-headed rice borer (Chilo polychrysus Meyrick), cabbage clustercaterpillar (Crocidolomia binotalis English)); leafrollers, budworms,seed worms, and fruit worms in the family Tortricidae (e.g., codlingmoth (Cydia pomonella Linnaeus), grape berry moth (Endopiza vireanaClemens), oriental fruit moth (Grapholita molesta Busck), citrus falsecodling moth (Cryprophlebia leucotreta Meyrick), citrus borer(Ecdytolopha aurantiana Lima), redbanded leafroller (Argyrotaeniavelutinana Walker), obliquebanded leafroller (Choristoneura rosaceanaHarris), light brown apple moth (Epiphyas postvittana Walker), Europeangrape berry moth (Eupoecilia ambiguella Hübner), apple bud moth(Pandemis pyrusana Kearfott), omnivorous leafroller (Platynota stultanaWalsingham), barred fruit-tree tortrix (Pandemis cerasana Hübner), applebrown tortrix (Pandemis heparana Denis & Schiffermüller)); and manyother economically important lepidoptera (e.g., diamondback moth(Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiellaSaunders), gypsy moth (Lymantria dispar Linnaeus), peach fruit borer(Carposina niponensis Walsingham), peach twig borer (Anarsia lineatellaZeller), potato tuberworm (Phthorimaea operculella Zeller), spottedteniform leafminer (Lithocolletis blancardella Fabricius), Asiatic appleleafminer (Lithocolletis ringoniella Matsumura), rice leaffolder(Lerodea eufala Edwards); apple leafminer (Leucoptera scitella Zeller));eggs, nymphs and adults of the order Blattodea including cockroachesfrom the families Blattellidae and Blattidae (e.g., oriental cockroach(Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinaiMizukubo), German cockroach (Blattella germanica Linnaeus), brownbandedcockroach (Supella longipalpa Fabricius), American cockroach(Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunneaBurmeister), Madeira cockroach (Leucophaea maderae Fabricius)), smokybrown cockroach (Periplaneta fuliginosa Service), Australian Cockroach(Periplaneta australasiae Fabr.), lobster cockroach (Nauphoeta cinereaOlivier) and smooth cockroach (Symplace pallens Stephens)); eggs, foliarfeeding, fruit feeding, root feeding, seed feeding and vesicular tissuefeeding larvae and adults of the order Coleoptera including weevils fromthe families Anthribidae, Bruchidae, and Curculionidae (e.g., bollweevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrusoryzophilus Kuschel), granary weevil (Sitophilus granaries Linnaeus),rice weevil (Sitophilus oryzae Linnaeus)), annual bluegrass weevil(Listronotus maculicollis Dietz), bluegrass bilibug (Sphenophorusparvulus Gyllenhal), hunting bilibug (Sphenophorus venatus vestitus),Denver bilibug (Sphenophorus cicatristriatus Fahraeus)); flea beetles,cucumber beetles, rootworms, leaf beetles, potato beetles, andleafminers in the family Chrysomelidae (e.g., Colorado potato beetle(Leptinotarsa decemlineata Say), western corn rootworm (Diabroticavirgifera virgifera LeConte)); chafers and other beetles from the familyScarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), orientalbeetle (Anomala orientalis Waterhouse, Exomala orientalis (Waterhouse)Baraud), northern masked chafer (Cyclocephala borealis Arrow), southernmasked chafer (Cyclocephala immaculata Olivier or C. lurida Bland) dungbeetle and white grub (Aphodius spp.), black turfgrass ataenius(Ataenius spretulus Haldeman), green June beetle (Cotinis nitidaLinnaeus), Asiatic garden beetle (Maladera castanea Arrow), May/Junebeetles (Phyllophaga spp.) and European chafer (Rhizotrogus majalisRazoumowsky)); carpet beetles from the family Dermestidae; wirewormsfrom the family Elateridae; bark beetles from the family Scolytidae andflour beetles from the family Tenebrionidae. In addition, agronomic andnonagronomic pests include: eggs, adults and larvae of the orderDermaptera including earwigs from the family Forficulidae (e.g.,European earwig (Forficula auricularia Linnaeus), black earwig(Chelisoches morio Fabricius)); eggs, immatures, adults and nymphs ofthe orders Hemiptera and Homoptera such as, plant bugs from the familyMiridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoascaspp.) from the family Cicadellidae, bed bugs (e.g., Cimex lectulariusLinnaeus) from the family Cimicidae, planthoppers from the familiesFulgoroidae and Delphacidae, treehoppers from the family Membracidae,psyllids from the family Psyllidae, whiteflies from the familyAleyrodidae, aphids from the family Aphididae, phylloxera from thefamily Phylloxeridae, mealybugs from the family Pseudococcidae, scalesfrom the families Coccidae, Diaspididae and Margarodidae, lace bugs fromthe family Tingidae, stink bugs from the family Pentatomidae, chinchbugs (e.g., hairy chinch bug (Blissus leucopterus hircus Montandon) andsouthern chinch bug (Blissus insularis Barber)) and other seed bugs fromthe family Lygaeidae, spittlebugs from the family Cercopidae squash bugsfrom the family Coreidae, and red bugs and cotton stainers from thefamily Pyrrhocoridae. Also included are eggs, larvae, nymphs and adultsof the order Acari (mites) such as spider mites and red mites in thefamily Tetranychidae (e.g., European red mite (Panonychus ulmi Koch),two spotted spider mite (Tetranychus urticae Koch), McDaniel mite(Tetranychus mcdanieli McGregor)); flat mites in the familyTenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor));rust and bud mites in the family Eriophyidae and other foliar feedingmites and mites important in human and animal health, i.e. dust mites inthe family Epidermoptidae, follicle mites in the family Demodicidae,grain mites in the family Glycyphagidae, ticks in the order Ixodidae(e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick(Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilisSay), lone star tick (Amblyomma americanum Linnaeus)) and scab and itchmites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; eggs,adults and immatures of the order Orthoptera including grasshoppers,locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplussanguinipes Fabricius, M. differentialis Thomas), American grasshoppers(e.g., Schistocerca americana Drury), desert locust (Schistocercagregaria Forskal), migratory locust (Locusta migratoria Linnaeus), bushlocust (Zonocerus spp.), house cricket (Acheta domesticus Linnaeus),mole crickets (e.g., tawny mole cricket (Scapteriscus vicinus Scudder)and southern mole cricket (Scapteriscus borellii Giglio-Tos)); eggs,adults and immatures of the order Diptera including leafminers (e.g.,Liriomyza spp. such as serpentine vegetable leafminer (Liriomyza sativaeBlanchard)), midges, fruit flies (Tephritidae), frit flies (e.g.,Oscinella frit Linnaeus), soil maggots, house flies (e.g., Muscadomestica Linnaeus), lesser house flies (e.g., Fannia canicularisLinnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitransLinnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp.,Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanusspp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.); cattle grubs(e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g.,Melophagus ovines Linnaeus) and other Brachycera, mosquitoes (e.g.,Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimuliumspp., Simulium spp.), biting midges, sand flies, sciarids, and otherNematocera; eggs, adults and immatures of the order Thysanopteraincluding onion thrips (Thrips tabaci Lindeman), flower thrips(Frankliniella spp.), and other foliar feeding thrips; insect pests ofthe order Hymenoptera including ants of the Family Formicidae includingthe Florida carpenter ant (Camponotus floridanus Buckley), red carpenterant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotuspennsylvanicus De Geer), white-footed ant (Techndmyrmex albipes fr.Smith), big headed ants (Pheidole sp.), ghost ant (Tapinomamelanocephalum Fabricius); Pharaoh ant (Monomorium pharaonis Linnaeus),little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsisgeminata Fabricius), red imported fire ant (Solenopsis invicta Buren),Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechinalongicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus),cornfield ant (Lasius alienus Förster) and odorous house ant (Tapinomasessile Say). Other Hymenoptera including bees (including carpenterbees), hornets, yellow jackets, wasps, and sawflies (Neodiprion spp.;Cephus spp.); insect pests of the order Isoptera including termites inthe Termitidae (e.g., Macrotermes sp., Odontotermes obelus Rambur),Kalotermitidae (e.g., Cryptotermes sp.), and Rhinotermitidae (e.g.,Reticulitermes sp., Coptotermes sp., Heterotermes tenuis Hagen)families, the eastern subterranean teunite (Reticulitermes flavipesKollar), western subterranean termite (Reticulitermes hesperus Banks),Formosan subterranean termite (Coptotermes formosanus Shiraki), WestIndian drywood termite (Incisitermes immigrans Snyder), powder posttermite (Cryptotermes brevis Walker), drywood termite (Incisitermessnyderi Light), southeastern subterranean termite (Reticulitermesvirginicus Banks), western drywood termite (Incisitermes minor Hagen),arboreal termites such as Nasutitermes sp. and other termites ofeconomic importance; insect pests of the order Thysanura such assilverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobiadomestica Packard); insect pests of the order Mallophaga and includingthe head louse (Pediculus humanus capitis De Geer), body louse(Pediculus humanus Linnaeus), chicken body louse (Menacanthus stramineusNitszch), dog biting louse (Trichodectes canis De Geer), fluff louse(Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank),short-nosed cattle louse (Haematopinus eurysternus Nitzsch), long-nosedcattle louse (Linognathus vituli Linnaeus) and other sucking and chewingparasitic lice that attack man and animals; insect pests of the orderSiphonoptera including the oriental rat flea (Xenopsylla cheopisRothschild), cat flea (Ctenocephalides fells Bouche), dog flea(Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinaeSchrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea(Pulex irritans Linnaeus) and other fleas afflicting mammals and birds.Additional arthropod pests covered include: spiders in the order Araneaesuch as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik)and the black widow spider (Latrodectus mactans Fabricius), andcentipedes in the order Scutigeromorpha such as the house centipede(Scutigera coleoptrata Linnaeus). Compounds of the present inventionalso have activity on members of the Classes Nematoda, Cestoda,Trematoda, and Acanthocephala including economically important membersof the orders Strongylida, Ascaridida, oxyurida, Rhabditida, Spirurida,and Enoplida such as but not limited to economically importantagricultural pests (i.e. root knot nematodes in the genus Meloidogyne,lesion nematodes in the genus Pratylenchus, stubby root nematodes in thegenus Trichodorus, etc.) and animal and human health pests (i.e. alleconomically important flukes, tapeworms, and roundworms, such asStrongylus vulgaris in horses, Toxocara canis in dogs, Haemonchuscontortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephalaperfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

Compounds of the invention show particularly high activity against pestsin the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit tree leaf roller), A. rosanaLinnaeus (European leaf roller) and other Archips species, Chilosuppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenée(rice leaf roller), Crambus caliginosellus Clemens (corn root webworm),Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonellaLinnaeus (codling moth), Earias insulana Boisduval (spiny bollworm),Earias vittella Fabricius (spotted bollworm), Helicoverpa armigeraHübner (American bollworm), Helicoverpa zea Boddie (corn earworm),Heliothis virescens Fabricius (tobacco budworm), Herpetogrammalicarsisalis Walker (sod webworm), Lobesia botrana Denis &Schiffermüller (grape berry moth), Pectinophora gossypiella Saunders(pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer),Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus(small white butterfly), Plutella xylostella Linnaeus (diamondbackmoth), Spodoptera exigua Hübner (beet armyworm), Spodoptera lituraFabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperdaJ. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) andTuta absoluta Meyrick (tomato leafminer)).

Compounds of the invention also have significant activity on membersfrom the order Homoptera including: Acyrthosiphon pisum Harris (peaaphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (blackbean aphid), Aphis gossypii Gloyer (cotton aphid, melon aphid), Aphispomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid),Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefoliiCockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko(Russian wheat aphid); Dysaphis plantaginea Paaserini (rosy appleaphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopteruspruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnipaphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosiphumeuphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potatoaphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid),Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch(corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid),Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius(English grain aphid), Therioaphis maculata Buckton (spotted alfalfaaphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid),and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp.(adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisiatabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisiaargentifolii Bellows & Pelting (silverleaf whitefly), Dialeurodes citriAshmead (citrus whitefly) and Trialeurodes vaporariorum Westwood(greenhouse whitefly); Empoasca fabae Harris (potato leafhopper),Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestesquadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler(green leafhopper), Nephotettix nigropictus Seal (rice leafhopper),NilaParvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead(corn planthopper), Sogatella furcifera Horvath (white-backedplanthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocybapomaria McAtee white apple leafhopper, Erythroneoura spp. (grapeleafhoppers); Magicidada septendecim Linnaeus (periodical cicada);Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotusperniciosus Comstock (San Jose scale); Planococcus citri Risso (citrusmealybug); Pseudococcus spp. (other mealybug complex); Cacopsyllapyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmonpsylla).

Compounds of this invention also have activity on members from the orderHemiptera including: Acrosternum hilare Say (green stink bug), Anasatristis De Geer (squash bug), Blissus leucopterus leucopterus Say(chinch bug), Cimex lectularius Linnaeus (bed bug) Corythuca gossypiiFabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug),Dysdercus suturellus Herrich-Schäffer (cotton stainer), Euchistus servusSay (brown stink bug), Euchistus variolarius Palisot de Beauvois(one-spotted stink bug), Graptosthetus spp. (complex of seed bugs),Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolarisPalisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus(southern green stink bug), Oebalus pugnax Fabricius (rice stink bug),Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelisseriatus Reuter (cotton fleahopper). Other insect orders controlled bycompounds of the invention include Thysanoptera (e.g., Frankliniellaoccidentalis Pergande (western flower thrips), Scirthothrips citriMoulton (citrus thrips), Sericothrips variabilis Beach (soybean thrips),and Thrips tabaci Lindeman (onion thrips); and the order Coleoptera(e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachnavarivestis Mulsant (Mexican bean beetle) and wireworms of the generaAgriotes, Athous or Limonius).

Note that some contemporary classification systems place Homoptera as asuborder within the order Hemiptera.

Of note is use of compounds of this invention for controlling silverleafwhitefly (Bemisia argentifolii). Of note is use of compounds of thisinvention for controlling western flower thrips (Frankliniellaoccidentalis). Of note is use of compounds of this invention forcontrolling potato leafhopper (Empoasca fabae). Of note is use ofcompounds of this invention for controlling corn planthopper (Peregrinusmaidis). Of note is use of compounds of this invention for controllingcotton melon aphid (Aphis gossypii). Of note is use of compounds of thisinvention for controlling green peach aphid (Myzus persicae). Of note isuse of compounds of this invention for controlling diamondback moth(Plutella xylostella). Of note is use of compounds of this invention forcontrolling fall armyworm (Spodoptera frugiperda).

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including insecticides,fungicides, nematocides, bactericides, acaricides, herbicides, growthregulators such as rooting stimulants, chemosterilants, semiochemicals,repellents, attractants, pheromones, feeding stimulants, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agronomic and nonagronomic utility. Thus the presentinvention also pertains to a composition comprising a biologicallyeffective amount of a compound of Formula 1, an N-oxide or salt thereof,and an effective amount of at least one additional biologically activecompound or agent and can further comprise at least one of a surfactant,a solid diluent or a liquid diluent. The other biologically activecompounds or agents can be formulated in compositions comprising atleast one of a surfactant, solid or liquid diluent. For mixtures of thepresent invention, the other biologically active compounds or agents canbe formulated together with the present compounds, including thecompounds of Formula 1, to form a premix, or the other biologicallyactive compounds or agents can be formulated separately from the presentcompounds, including the compounds of Formula 1, and the twoformulations combined together before application (e.g., in a spraytank) or, alternatively, applied in succession.

Other biologically active compounds or agents useful in the compositionsof the present invention can be selected from invertebrate pest controlagents having a different mode of action or a different chemical classincluding macrocyclic lactones, neonicotinoids, octopamine receptorligands, ryanodine receptor ligands, ecdysone agonists, sodium channelmodulators, chitin synthesis inhibitors, nereisotoxin analogs,mitochondrial electron transport inhibitors, cholinesterase inhibitors,cyclodiene insecticides, molting inhibitors, GABA (γ-aminobutyricacid)-regulated chloride channel blockers, juvenile hormone mimics,lipid biosynthesis inhibitors and biological agents includingnucleopolyhedrovirus (NPV), a member of Bacillus thuringiensis, anencapsulated delta-endotoxin of Bacillus thuringiensis; and a naturallyoccurring or a genetically modified viral insecticide. Of note areadditional biologically active compounds or agents selected frominsecticides of the group consisting of pyrethroids, carbamates,neonicotinoids, neuronal sodium channel blockers, insecticidalmacrocyclic lactones, γ-aminobutyric acid antagonists, insecticidalureas and juvenile hormone mimics, a member of Bacillus thuringiensis, aBacillus thuringiensis delta-endotoxin, and a naturally occurring or agenetically modified viral insecticide.

Of note is a composition of the present invention wherein at least oneadditional biologically active compound or agent is selected frominsecticides of the group consisting of macrocyclic lactones,neonicotinoids, octopamine receptor ligands, ryanodine receptor ligands,ecdysone agonists, sodium channel modulators, chitin synthesisinhibitors, nereisotoxin analogs, mitochondrial electron transportinhibitors, cholinesterase inhibitors, cyclodiene insecticides, moltinginhibitors, GABA-regulated chloride channel blockers, juvenile hormonemimics, biological agents, and lipid biosynthesis inhibitors.

Examples of such biologically active compounds or agents with whichcompounds of this invention can be formulated are: insecticides such asabamectin, acephate, acetamiprid, acetoprole, amidoflumet (S-1955),avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate,bistrifluoron, buprofezin, carbofuran, cartap, chlorfenapyr,chlorfluazuron; chlorantraniliprole (DPX-E2Y45), chlorpyrifos,chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen,cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin,lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin,dimethoate, dinotefuran, diofenolan, emamectin, endosulfan,esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin,fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate,tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos,halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,metofluthrin, monocrotophos, methoxyfenozide, monocrotophos, nitenpyram,nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion,parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,pirimicarb, profenofos, profluthrin, protrifenbute, pymetrozine,pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole,pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen,spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin,triazamate, trichlorfon and triflumuron; fungicides such as acibenzolar,aldimorph, amisulbrom, azaconazole, azoxystrobin, benalaxyl, benomyl,benthiavalicarb, benthiavalicarb-isopropyl, binomial, biphenyl,bitertanol, blasticidin-S, Bordeaux mixture (Tribasic copper sulfate),boscalid/nicobifen, bromuconazole, bupirimate, buthiobate, carboxin,carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil,chlozolinate, clotrimazole, copper oxychloride, copper salts such ascopper sulfate and copper hydroxide, cyazofamid, cyflunamid, cymoxanil,cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine,dicloran, diethofencarb, difenoconazole, dimethomorph, dinioxystrobin,diniconazole, diniconazole-M, dinocap; discostrobin, dithianon,dodemorph, dodine, econazole, etaconazole, edifenphos, epoxiconazole,ethaboxam, ethirimol, ethridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid, fenfuram, fenhexamide, fenoxanil,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferfurazoate, ferimzone, fluazinam, fludioxonil,flumetover, fluopicolide, fluoxastrabin, fluquinconazole,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol,folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametapyr,hexaconazole, hymexazole, guazatine, imazalil, imibenconazole,iminoctadine, iodicarb, ipconazole, iprobenfos, iprodione, iprovalicarb,isoconazole, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb,mandipropamid, maneb, mapanipyrin, mefenoxam, mepronil, metalaxyl,metconazole, methasulfocarb, metiram, metominostrobin/fenominostrobin,mepanipyrim, metrafenone, miconazole, myclobutanil, neo-asozin (ferricmethanearsonate), nuarimol, octhilinone, ofurace, orysastrobin,oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, paclobutrazol,penconazole, pencycuron, penthiopyrad, perfurazoate, phosphonic acid,phthalide, picobenzamid, picoxystrobin, polyoxin, probenazole,prochloraz, procymidone, propamocarb, propamocarb-hydrochloride,propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin,pryazophos, pyrifenox, pyrimethanil, pyrifenox, pyrolnitrine,pyroquilon, quinconazole, quinoxyfen, quinfozene, silthiofam,simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole,techrazene, tecloftalam, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil,tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, triarimol,triazoxide, tridemorph, trimoprhamide tricyclazole, trifloxystrobin,triforine, triticonazole, uniconazole, validamycin, vinclozolin, zineb,ziram, and zoxamide; nematocides such as aldicarb, imicyafos, oxamyl andfenamiphos; bactericides such as streptomycin; acaricides such asamitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; andbiological agents including entomopathogenic bacteria, such as Bacillusthuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki,and the encapsulated delta-endotoxins of Bacillus thuringiensis (e.g.,Cellcap, MPV, MPVII); entomopathogenic fungi, such as green muscardinefungus; and entomopathogenic virus including baculovirus,nucleopolyhedrovirus (NPV) such as Helicoverpa zea nucleopolyhedrovirus(HzNPV), Anagrapha falcifera nucleopolyhedrovirus (AfNPV); andgranulosis virus (GV) such as Cydia pomonella granulosis virus (CpGV).

Compounds of this invention and compositions thereof can be applied toplants genetically transformed to express proteins toxic to invertebratepests (such as Bacillus thuringiensis delta-endotoxins). The effect ofthe exogenously applied invertebrate pest control compounds of thisinvention may be synergistic with the expressed toxin proteins.

General references for these agricultural protectants (i.e.insecticides, fungicides, nematocides, acaricides, herbicides andbiological agents) include The Pesticide Manual, 13th Edition, C. D. S.Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K.,2003 and The BioPesticide Manual, 2^(nd) Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2001.

Of note is a composition of the present invention wherein at least oneadditional biologically active compound or agent is selected from thegroup consisting of abamectin, acephate, acetamiprid, acetoprole,aldicarb, amidoflumet, amitraz, avermectin, azadirachtin,azinphos-methyl, bifenthrin, bifenazate, bistrifluoron, buprofezin,carbofuran, cartap, chinomethionat, chlorfenapyr, chlorfluazuron,chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, chlorobenzilate,chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin,cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyhexatin,cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon,dicofol, dieldrin, dienochlor, diflubenzuron, dimefluthrin, dimethoate,dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate,ethiprole, etoxazole, fenamiphos, fenazaquin, fenbutatin oxide,fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenvalerate,fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate,flufenerim, flufenoxuron; fonophos, halofenozide, hexaflumuron,hexythiazox, hydramethylnon, imicyafos, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine,novaluron, noviflumuron, oxamyl, parathion, parathion-methyl,permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,profenofos, profluthrin, propargite, protrifenbute, pymetrozine,pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazom,pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad,spiridiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos,tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos,tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb,thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus, an encapsulateddelta-endotoxin of Bacillus thuringiensis, baculovirus, entomopathogenicbacteria, entomopathogenic virus and entomopathogenic fungi.

Of particular note is a composition of the present invention wherein theat least one additional biologically active compound or agent isselected from the group consisting of abamectin, acephate, acetamiprid,acetoprole, amidoflumet, avermectin, azadirachtin, azinphos-methyl,bifenthrin, bifenazate, bistrifluoron, buprofezin, carbofuran, cartap,chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl,chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin,cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin,dimethoate, dinotefuran, diofenolan, emamectin, endosulfan,esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin,fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate,tau-fluvalinate, flufenerim, flufenoxuron, fonophos, gamma-cyhalothrin,halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine,novaluron, noviflumuron, oxamyl, parathion, parathion-methyl,permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,profenofos, profluthrin, protrifenbute, pymetrozine, pyrafluprole,pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen,rotenone, ryanodine, S1812 (Valent), spinosad, spiridiclofen,spiromesifen, spirotetramat, sulprofos, tebufenozide, teflubenzuron,tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam,thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate,trichlorfon, triflumuron, aldicarb, imicyafos, fenamiphos, amitraz,chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor,etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate,hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensisaizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis deltaendotoxin, baculovirus, entomopathogenic bacteria, entomopathogenicvirus and entomopathogenic fungi.

Also of note is a composition of the present invention wherein at leastone additional biologically active compound or agent is selected fromthe group consisting of abamectin, acetamiprid, amitraz, avermectin,azadirachtin, bifenthrin, buprofezin, cartap, chlorantraniliprole,chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin,cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,dieldrin, dinotefuran, diofenolan, emamectin; endosulfan, esfenvalerate,ethiprole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid,flubendiamide, flufenoxuron; hexaflumuron, hydramethylnon, imidacloprid,indoxacarb, lufenuron, metaflumizone, methomyl, methoprene,methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine,pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram,spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus and an encapsulateddelta-endotoxin of Bacillus thuringiensis.

Of further note is a composition of the present invention wherein the atleast one additional biologically active compound or agent is selectedfrom the group consisting of abamectin, acetamiprid, amitraz, ananthranilic diamide, avermectin, azadirachtin, beta-cyfluthrin,bifenthrin, buprofezin, cartap, chlorfenapyr, chlorpyrifos,clothianidin, cyfluthrin, cyhalothrin, cypermethrin, cyromazine,deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, emamectinbenzoate, endosulfan, esfenvalerate, tethiprole, fenothiocarb,fenoxycarb, fenvalerate, fipronil, flonicamid, flufenoxuron,hexaflumuron, hydramethylnon, imidacloprid, indoxacarb,lambda-cyhalothrin, lufenuron, metaflumizone, methomyl, methoprene,methoxyfenozide, nitenpyram, nithiazine, novaluron, NPR, oxamyl,pymetrozine, pyrethrin, pyridaben, pyridalyl, priproxyfen, ryanodine,spinosal, spirodiclofen, spiromesifen, tebufenozide, thiacloprid,thiamethoxam, thiodicarb, tralomethrin, triazamate, triflumuron,Bacillus thuringiensis, Bacillus thuringiensis delta toxin, andBeauvaria bassiana.

For embodiments where one or more of these various mixing partners areused, the weight ratio of these various mixing partners (in total) tothe compound of Formula 1 is typically between about 1:3000 and about3000:1. Of note are weight ratios between about 1:300 and about 300:1(for example ratios between about 1:30 and about 30:1). One skilled inthe art can easily determine through simple experimentation thebiologically effective amounts of active ingredients necessary for thedesired spectrum of biological activity. It will be evident thatincluding these additional components may expand the spectrum ofinvertebrate pests controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly invertebrate pest control)compounds or agents (i.e. active ingredients) can result in agreater-than-additive (i.e. synergistic) effect. Reducing the quantityof active ingredients released in the environment while ensuringeffective pest control is always desirable. When synergism ofinvertebrate pest control active ingredients occurs at application ratesgiving agronomically satisfactory levels of invertebrate pest control,such combinations can be advantageous for reducing crop production costand decreasing environmental load.

Of note is a combination of a compound of Formula 1 with at least oneother invertebrate pest control active ingredient. Of particular note issuch a combination where the other invertebrate pest control activeingredient has different site of action from the compound of Formula 1.In certain instances, a combination with at least one other invertebratepest control active ingredient having a similar spectrum of control buta different site of action will be particularly advantageous forresistance management. Thus, a composition of the present invention canfurther comprise a biologically effective amount of at least oneadditional invertebrate pest control active ingredient having a similarspectrum of control but a different site of action. Contacting a plantgenetically modified to express an invertebrate pest compound (e.g.,protein) or the locus of the plant with a biologically effective amountof a compound of this invention can also provide a broader spectrum ofplant protection and be advantageous for resistance management.

Table A lists specific combinations of a compound of Formula 1 withother invertebrate pest control agents illustrative of the mixtures,compositions and methods of the present invention. The first column ofTable A lists the specific invertebrate pest control agents (e.g.,“Abamectin” in the first line). The second column of Table A lists themode of action (if known) or chemical class of the invertebrate pestcontrol agents. The third column of Table A lists embodiment(s) ofranges of weight ratios for rates at which the invertebrate pest controlagent can be applied relative to a compound of Formula 1, an N-oxide, ora salt thereof, (e.g., “50:1 to 1:50” of abamectin relative to acompound of Formula 1 by weight). Thus, for example, the first line ofTable A specifically discloses the combination of a compound of Formula1 with abamectin can be applied in a weight ratio between 50:1 to 1:50.The remaining lines of Table A are to be construed similarly. Of furthernote Table A lists specific combinations of a compound of Formula 1 withother invertebrate pest control agents illustrative of the mixtures,compositions and methods of the present invention and includesadditional embodiments of weight ratio ranges for application rates.

TABLE A Invertebrate Pest Mode of Action or Typical Control AgentChemical Class Weight Ratio Abamectin macrocyclic lactones 50:1 to 1:50Acetamiprid neonicotinoids 150:1 to 1:200 Amitraz octopamine receptorligands 200:1 to 1:100 Avermectin macrocyclic lactones 50:1 to 1:50Azadirachtin ecdysone agonists 100:1 to 1:120 Beta-cyfluthrin sodiumchannel modulators 150:1 to 1:200 Bifenthrin sodium channel modulators100:1 to 1:10 Buprofezin chitin synthesis inhibitors 500:1 to 1:50Cartap nereistoxin analogs 100:1 to 1:200 Chlorantraniliprole ryanodinereceptor ligands 100:1 to 1:120 Chlorfenapyr mitochondrial electron300:1 to 1:200 transport inhibitors Chlorpyrifos cholinesteraseinhibitors 500:1 to 1:200 Clothianidin neonicotinoids 100:1 to 1:400Cyfluthrin sodium channel modulators 150:1 to 1:200 Cyhalothrin sodiumchannel modulators 150:1 to 1:200 Cypermethrin sodium channel modulators150:1 to 1:200 Cyromazine chitin synthesis inhibitors 400:1 to 1:50Deltamethrin sodium channel modulators 50:1 to 1:400 Dieldrin cyclodieneinsecticides 200:1 to 1:100 Dinotefuran neonicotinoids 150:1 to 1:200Diofenolan molting inhibitor 150:1 to 1:200 Emamectin macrocycliclactones 50:1 to 1:10 Endosulfan cyclodiene insecticides 200:1 to 1:100Esfenvalerate sodium channel modulators 100:1 to 1:400 EthiproleGABA-regulated chloride 200:1 to 1:100 channel blockers Fenothiocarb150:1 to 1:200 Fenoxycarb juvenile hormone mimics 500:1 to 1:100Fenvalerate sodium channel modulators 150:1 to 1:200 FipronilGABA-regulated chloride 150:1 to 1:100 channel blockers Flonicamid 200:1to 1:100 Flubendiamide ryanodine receptor ligands 100:1 to 1:120Flufenoxuron chitin synthesis inhibitors 200:1 to 1:100 Hexaflumuronchitin synthesis inhibitors 300:1 to 1:50 Hydramethylnon mitochondrialelectron 150:1 to 1:250 transport inhibitors Imidacloprid neonicotinoids1000:1 to 1:1000 Indoxacarb sodium channel modulators 200:1 to 1:50Lambda-cyhalothrin sodium channel modulators 50:1 to 1:250 Lufenuronchitin synthesis inhibitors 500:1 to 1:250 Metaflumizone 200:1 to 1:200Methomyl cholinesterase inhibitors 500:1 to 1:100 Methoprene juvenilehormone mimics 500:1 to 1:100 Methoxyfenozide ecdysone agonists 50:1 to1:50 Nitenpyram neonicotinoids 150:1 to 1:200 Nithiazine neonicotinoids150:1 to 1:200 Novaluron chitin synthesis inhibitors 500:1 to 1:150Oxamyl cholinesterase inhibitors 200:1 to 1:200 Pymetrozine 200:1 to1:100 Pyrethrin sodium channel modulators 100:1 to 1:10 Pyridabenmitochondrial electron 200:1 to 1:100 transport inhibitors Pyridalyl200:1 to 1:100 Pyriproxyfen juvenile hormone mimics 500:1 to 1:100Ryanodine ryanodine receptor ligands 100:1 to 1:120 Spinetorammacrocyclic lactones 150:1 to 1:100 Spinosad macrocyclic lactones 500:1to 1:10 Spirodiclofen lipid biosynthesis inhibitors 200:1 to 1:200Spiromesifen lipid biosynthesis inhibitors 200:1 to 1:200 Tebufenozideecdysone agonists 500:1 to 1:250 Thiacloprid neonicotinoids 100:1 to1:200 Thiamethoxam neonicotinoids 1250:1 to 1:1000 Thiodicarbcholinesterase inhibitors 500:1 to 1:400 Thiosultap-sodium 150:1 to1:100 Tralomethrin sodium channel modulators 150:1 to 1:200 Triazamatecholinesterase inhibitors 250:1 to 1:100 Triflumuron chitin synthesisinhibitors 200:1 to 1:100 Bacillus thuringiensis biological agents 50:1to 1:10 Bacillus thuringiensis biological agents 50:1 to 1:10delta-endotoxin NPV (e.g., Gemstar) biological agents 50:1 to 1:10

One embodiment of invertebrate pest control agents (e.g., insecticidesand acaricides) for mixing with compounds of this invention includesodium channel modulators such as bifenthrin, cypermethrin, cyhalothrin,lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, deltamethrin,dimefluthrin, esfenvalerate, fenvalerate, indoxacarb, metofluthrin,profluthrin, pyrethrin and tralomethrin; cholinesterase inhibitors suchas chlorpyrifos, methomyl, oxamyl, thiodicarb and triazamate;neonicotinoids such as acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, nithiazine, thiacloprid and thiamethoxam;insecticidal macrocyclic lactones such as spinetoram, spinosad,abamectin, avermectin and emamectin; GABA (γ-aminobutyricacid)-regulated chloride channel blockers such as endosulfan, ethiproleand fipronil; chitin synthesis inhibitors such as buprofezin,cyromazine, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron and triflumuron; juvenile hormone mimics such asdiofenolan, fenoxycarb, methoprene and pyriproxyfen; octopamine receptorligands such as amitraz; ecdysone agonists such as azadirachtin,methoxyfenozide and tebufenozide; ryanodine receptor ligands such asryanodine, anthranilic diamides such as chlorantraniliprole (see U.S.Pat. No. 6,747,047, PCT Publications WO 2003/015518 and WO 2004/067528)and flubendiamide (see U.S. Pat. No. 6,603,044); nereistoxin analogssuch as cartap; mitochondrial electron transport inhibitors such aschlorfenapyr, hydramethylnon and pyridaben; lipid biosynthesisinhibitors such as spirodiclofen and spiromesifen; cyclodieneinsecticides such as dieldrin; cyflumetofen; fenothiocarb; flonicamid;metaflumizone; pyrafluprole; pyridalyl; pyriprole; pymetrozine;spirotetramat; and thiosultap-sodium. One embodiment of biologicalagents for mixing with compounds of this invention includenucleopolyhedrovirus such as HzNPV and AfNPV; Bacillus thuringiensis andencapsulated delta-endotoxins of Bacillus thuringiensis such as Cellcap,MPV and MPVII; as well as naturally occurring and genetically modifiedviral insecticides including members of the family Baculoviridae as wellas entomophagous fungi. Of note is the composition of the presentinvention wherein the at least one additional biologically activecompound or agent is selected from the Invertebrate Pest Control Agentslisted in Table A above. Also of note is the composition of the presentinvention wherein the at least one additional biologically activecompound or agent is selected from the group consisting of cypermethrin,cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate,tralomethrin, fenothiocarb, methomyl, oxamyl, thiodicarb, acetamiprid,clothianidin, imidacloprid, thiamethoxam, thiacloprid, indoxacarb,spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole,fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen,pymetrozine, amitraz, Bacillus thuringiensis aisawai, Bacillusthuringiensis kurstaki, Bacillus thuringiensis delta endotoxin andentomophagous fungi.

The weight ratios of a compound, including a compound of Formula 1, anN-oxide or a salt thereof, to the additional invertebrate pest controlagent typically are between 1000:1 and 1:1000, with one embodiment beingbetween 500:1 and 1:500, another embodiment being between 250:1 and1:200 and another embodiment being between 100:1 and 1:50.

Listed below in Table B are embodiments of specific compositionscomprising a compound of Formula 1 (compound numbers refer to compoundsin Index Tables A-D) and an additional invertebrate pest control agent.

TABLE B Mixture Comp. Invertebrate Pest Control Mixture Comp.Invertebrate Pest Control No. No. and Agent No. No. and Agent A-1 9 andAbamectin B-1 42 and Abamectin A-2 9 and Acetamiprid B-2 42 andAcetamiprid A-3 9 and Amitraz B-3 42 and Amitraz A-4 9 and AvermectinB-4 42 and Avermectin A-5 9 and Azadirachtin B-5 42 and Azadirachtin A-69 and Beta-cyfluthrin B-6 42 and Beta-cyfluthrin A-7 9 and BifenthrinB-7 42 and Bifenthrin A-8 9 and Buprofezin B-8 42 and Buprofezin A-9 9and Cartap B-9 42 and Cartap A-10 9 and Chlorantraniliprole B-10 42 andChlorantraniliprole A-11 9 and Chlorfenapyr B-11 42 and ChlorfenapyrA-12 9 and Chlorpyrifos B-12 42 and Chlorpyrifos A-13 9 and ClothianidinB-13 42 and Clothianidin A-14 9 and Cyfluthrin B-14 42 and CyfluthrinA-15 9 and Cyhalothrin B-15 42 and Cyhalothrin A-16 9 and CypermethrinB-16 42 and Cypermethrin A-17 9 and Cyromazine B-17 42 and CyromazineA-18 9 and Deltamethrin B-18 42 and Deltamethrin A-19 9 and DieldrinB-19 42 and Dieldrin A-20 9 and Dinotefuran B-20 42 and Dinotefuran A-219 and Diofenolan B-21 42 and Diofenolan A-22 9 and Emamectin B-22 42 andEmamectin A-23 9 and Endosulfan B-23 42 and Endosulfan A-24 9 andEsfenvalerate B-24 42 and Esfenvalerate A-25 9 and Ethiprole B-25 42 andEthiprole A-26 9 and Fenothiocarb B-26 42 and Fenothiocarb A-27 9 andFenoxycarb B-27 42 and Fenoxycarb A-28 9 and Fenvalerate B-28 42 andFenvalerate A-29 9 and Fipronil B-29 42 and Fipronil A-30 9 andFlonicamid B-30 42 and Flonicamid A-31 9 and Flubendiamide B-31 42 andFlubendiamide A-32 9 and Flufenoxuron B-32 42 and Flufenoxuron A-33 9and Hexaflumuron B-33 42 and Hexaflumuron A-34 9 and Hydramethylnon B-3442 and Hydramethylnon A-35 9 and Imidacloprid B-35 42 and ImidaclopridA-36 9 and Indoxacarb B-36 42 and Indoxacarb A-37 9 andLambda-cyhalothrin B-37 42 and Lambda-cyhalothrin A-38 9 and LufenuronB-38 42 and Lufenuron A-39 9 and Metaflumizone B-39 42 and MetaflumizoneA-40 9 and Methomyl B-40 42 and Methomyl A-41 9 and Methoprene B-41 42and Methoprene A-42 9 and Methoxyfenozide B-42 42 and MethoxyfenozideA-43 9 and Nitenpyram B-43 42 and Nitenpyram A-44 9 and Nithiazine B-4442 and Nithiazine A-45 9 and Novaluron B-45 42 and Novaluron A-46 9 andOxamyl B-46 42 and Oxamyl A-47 9 and Pymetrozine B-47 42 and PymetrozineA-48 9 and Pyrethrin B-48 42 and Pyrethrin A-49 9 and Pyridaben B-49 42and Pyridaben A-50 9 and Pyridalyl B-50 42 and Pyridalyl A-51 9 andPyriproxyfen B-51 42 and Pyriproxyfen A-52 9 and Ryanodine B-52 42 andRyanodine A-53 9 and Spinetoram B-53 42 and Spinetoram A-54 9 andSpinosad B-54 42 and Spinosad A-55 9 and Spirodiclofen B-55 42 andSpirodiclofen A-56 9 and Spiromesifen B-56 42 and Spiromesifen A-57 9and Tebufenozide B-57 42 and Tebufenozide A-58 9 and Thiacloprid B-58 42and Thiacloprid A-59 9 and Thiamethoxam B-59 42 and Thiamethoxam A-60 9and Thiodicarb B-60 42 and Thiodicarb A-61 9 and Thiosultap-sodium B-6142 and Thiosultap-sodium A-62 9 and Tralomethrin B-62 42 andTralomethrin A-63 9 and Triazamate B-63 42 and Triazamate A-64 9 andTriflumuron B-64 42 and Triflumuron A-65 9 and Bacillus thuringiensisB-65 42 and Bacillus thuringiensis A-66 9 and Bacillus thuringiensisB-66 42 and Bacillus thuringiensis delta-endotoxin delta-endotoxin A-679 and NPV (e.g., Gemstar) B-67 42 and NPV (e.g., Gemstar) C-1 107 andAbamectin D-1 208 and Abamectin C-2 107 and Acetamiprid D-2 208 andAcetamiprid C-3 107 and Amitraz D-3 208 and Amitraz C-4 107 andAvermectin D-4 208 and Avermectin C-5 107 and Azadirachtin D-5 208 andAzadirachtin C-6 107 and Beta-cyfluthrin D-6 208 and Beta-cyfluthrin C-7107 and Bifenthrin D-7 208 and Bifenthrin C-8 107 and Buprofezin D-8 208and Buprofezin C-9 107 and Cartap D-9 208 and Cartap C-10 107 andChlorantraniliprole D-10 208 and Chlorantraniliprole C-11 107 andChlorfenapyr D-11 208 and Chlorfenapyr C-12 107 and Chlorpyrifos D-12208 and Chlorpyrifos C-13 107 and Clothianidin D-13 208 and ClothianidinC-14 107 and Cyfluthrin D-14 208 and Cyfluthrin C-15 107 and CyhalothrinD-15 208 and Cyhalothrin C-16 107 and Cypermethrin D-16 208 andCypermethrin C-17 107 and Cyromazine D-17 208 and Cyromazine C-18 107and Deltamethrin D-18 208 and Deltamethrin C-19 107 and Dieldrin D-19208 and Dieldrin C-20 107 and Dinotefuran D-20 208 and Dinotefuran C-21107 and Diofenolan D-21 208 and Diofenolan C-22 107 and Emamectin D-22208 and Emamectin C-23 107 and Endosulfan D-23 208 and Endosulfan C-24107 and Esfenvalerate D-24 208 and Esfenvalerate C-25 107 and EthiproleD-25 208 and Ethiprole C-26 107 and Fenothiocarb D-26 208 andFenothiocarb C-27 107 and Fenoxycarb D-27 208 and Fenoxycarb C-28 107and Fenvalerate D-28 208 and Fenvalerate C-29 107 and Fipronil D-29 208and Fipronil C-30 107 and Flonicamid D-30 208 and Flonicamid C-31 107and Flubendiamide D-31 208 and Flubendiamide C-32 107 and FlufenoxuronD-32 208 and Flufenoxuron C-33 107 and Hexaflumuron D-33 208 andHexaflumuron C-34 107 and Hydramethylnon D-34 208 and HydramethylnonC-35 107 and Imidacloprid D-35 208 and Imidacloprid C-36 107 andIndoxacarb D-36 208 and Indoxacarb C-37 107 and Lambda-cyhalothrin D-37208 and Lambda-cyhalothrin C-38 107 and Lufenuron D-38 208 and LufenuronC-39 107 and Metaflumizone D-39 208 and Metaflumizone C-40 107 andMethomyl D-40 208 and Methomyl C-41 107 and Methoprene D-41 208 andMethoprene C-42 107 and Methoxyfenozide D-42 208 and MethoxyfenozideC-43 107 and Nitenpyram D-43 208 and Nitenpyram C-44 107 and NithiazineD-44 208 and Nithiazine C-45 107 and Novaluron D-45 208 and NovaluronC-46 107 and Oxamyl D-46 208 and Oxamyl C-47 107 and Pymetrozine D-47208 and Pymetrozine C-48 107 and Pyrethrin D-48 208 and Pyrethrin C-49107 and Pyridaben D-49 208 and Pyridaben C-50 107 and Pyridalyl D-50 208and Pyridalyl C-51 107 and Pyriproxyfen D-51 208 and Pyriproxyfen C-52107 and Ryanodine D-52 208 and Ryanodine C-53 107 and Spinetoram D-53208 and Spinetoram C-54 107 and Spinosad D-54 208 and Spinosad C-55 107and Spirodiclofen D-55 208 and Spirodiclofen C-56 107 and SpiromesifenD-56 208 and Spiromesifen C-57 107 and Tebufenozide D-57 208 andTebufenozide C-58 107 and Thiacloprid D-58 208 and Thiacloprid C-59 107and Thiamethoxam D-59 208 and Thiamethoxam C-60 107 and Thiodicarb D-60208 and Thiodicarb C-61 107 and Thiosultap-sodium D-61 208 andThiosultap-sodium C-62 107 and Tralomethrin D-62 208 and TralomethrinC-63 107 and Triazamate D-63 208 and Triazamate C-64 107 and TriflumuronD-64 208 and Triflumuron C-65 107 and Bacillus thuringiensis D-65 208and Bacillus thuringiensis C-66 107 and Bacillus thuringiensis D-66 208and Bacillus thuringiensis delta-endotoxin delta-endotoxin C-67 107 andNPV (e.g., Gemstar) D-67 208 and NPV (e.g., Gemstar) E-1 65 andAbamectin F-1 69 and Abamectin E-2 65 and Acetamiprid F-2 69 andAcetamiprid E-3 65 and Amitraz F-3 69 and Amitraz E-4 65 and AvermectinF-4 69 and Avermectin E-5 65 and Azadirachtin F-5 69 and AzadirachtinE-6 65 and Beta-cyfluthrin F-6 69 and Beta-cyfluthrin E-7 65 andBifenthrin F-7 69 and Bifenthrin E-8 65 and Buprofezin F-8 69 andBuprofezin E-9 65 and Cartap F-9 69 and Cartap E-10 65 andChlorantraniliprole F-10 69 and Chlorantraniliprole E-11 65 andChlorfenapyr F-11 69 and Chlorfenapyr E-12 65 and Chlorpyrifos F-12 69and Chlorpyrifos E-13 65 and Clothianidin F-13 69 and Clothianidin E-1465 and Cyfluthrin F-14 69 and Cyfluthrin E-15 65 and Cyhalothrin F-15 69and Cyhalothrin E-16 65 and Cypermethrin F-16 69 and Cypermethrin E-1765 and Cyromazine F-17 69 and Cyromazine E-18 65 and Deltamethrin F-1869 and Deltamethrin E-19 65 and Dieldrin F-19 69 and Dieldrin E-20 65and Dinotefuran F-20 69 and Dinotefuran E-21 65 and Diofenolan F-21 69and Diofenolan E-22 65 and Emamectin F-22 69 and Emamectin E-23 65 andEndosulfan F-23 69 and Endosulfan E-24 65 and Esfenvalerate F-24 69 andEsfenvalerate E-25 65 and Ethiprole F-25 69 and Ethiprole E-26 65 andFenothiocarb F-26 69 and Fenothiocarb E-27 65 and Fenoxycarb F-27 69 andFenoxycarb E-28 65 and Fenvalerate F-28 69 and Fenvalerate E-29 65 andFipronil F-29 69 and Fipronil E-30 65 and Flonicamid F-30 69 andFlonicamid E-31 65 and Flubendiamide F-31 69 and Flubendiamide E-32 65and Flufenoxuron F-32 69 and Flufenoxuron E-33 65 and Hexaflumuron F-3369 and Hexaflumuron E-34 65 and Hydramethylnon F-34 69 andHydramethylnon E-35 65 and Imidacloprid F-35 69 and Imidacloprid E-36 65and Indoxacarb F-36 69 and Indoxacarb E-37 65 and Lambda-cyhalothrinF-37 69 and Lambda-cyhalothrin E-38 65 and Lufenuron F-38 69 andLufenuron E-39 65 and Metaflumizone F-39 69 and Metaflumizone E-40 65and Methomyl F-40 69 and Methomyl E-41 65 and Methoprene F-41 69 andMethoprene E-42 65 and Methoxyfenozide F-42 69 and Methoxyfenozide E-4365 and Nitenpyram F-43 69 and Nitenpyram E-44 65 and Nithiazine F-44 69and Nithiazine E-45 65 and Novaluron F-45 69 and Novaluron E-46 65 andOxamyl F-46 69 and Oxamyl E-47 65 and Pymetrozine F-47 69 andPymetrozine E-48 65 and Pyrethrin F-48 69 and Pyrethrin E-49 65 andPyridaben F-49 69 and Pyridaben E-50 65 and Pyridalyl F-50 69 andPyridalyl E-51 65 and Pyriproxyfen F-51 69 and Pyriproxyfen E-52 65 andRyanodine F-52 69 and Ryanodine E-53 65 and Spinetoram F-53 69 andSpinetoram E-54 65 and Spinosad F-54 69 and Spinosad E-55 65 andSpirodiclofen F-55 69 and Spirodiclofen E-56 65 and Spiromesifen F-56 69and Spiromesifen E-57 65 and Tebufenozide F-57 69 and Tebufenozide E-5865 and Thiacloprid F-58 69 and Thiacloprid E-59 65 and Thiamethoxam F-5969 and Thiamethoxam E-60 65 and Thiodicarb F-60 69 and Thiodicarb E-6165 and Thiosultap-sodium F-61 69 and Thiosultap-sodium E-62 65 andTralomethrin F-62 69 and Tralomethrin E-63 65 and Triazamate F-63 69 andTriazamate E-64 65 and Triflumuron F-64 69 and Triflumuron E-65 65 andBacillus thuringiensis F-65 69 and Bacillus thuringiensis E-66 65 andBacillus thuringiensis F-66 69 and Bacillus thuringiensisdelta-endotoxin delta-endotoxin E-67 65 and NPV (e.g., Gemstar) F-67 69and NPV (e.g., Gemstar)

The specific mixtures listed in Table B typically combine a compound ofFormula 1 with the other invertebrate pest agent in the ratios specifiedin Table A.

Invertebrate pests are controlled in agronomic and nonagronomicapplications by applying one or more compounds of this invention,typically in the of a composition, in a biologically effective amount,to the environment of the pests, including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directlyon the pests to be controlled.

Thus the present invention comprises a method for controlling aninvertebrate pest in agronomic and/or nonagronomic applications,comprising contacting the invertebrate pest or its environment with abiologically effective amount of one or more of the compounds of theinvention, or with a composition comprising at least one such compoundor a composition comprising at least one such compound and abiologically effective amount of at least one additional biologicallyactive compound or agent. Examples of suitable compositions comprising acompound of the invention and a biologically effective amount of atleast one additional biologically active compound or agent includegranular compositions wherein the additional active compound is presenton the same granule as the compound of the invention or on granulesseparate from those of the compound of the invention.

To achieve contact with a compound or composition of the invention toprotect a field crop from invertebrate pests, the compound orcomposition is typically applied to the seed of the crop beforeplanting, to the foliage (e.g., leaves, stems, flowers, fruits) of cropplants, or to the soil or other growth medium before or after the cropis planted.

One embodiment of a method of contact is by spraying. Alternatively, agranular composition comprising a compound of the invention can beapplied to the plant foliage or the soil. Compounds of this inventioncan also be effectively delivered through plant uptake by contacting theplant with a composition comprising a compound of this invention appliedas a soil drench of a liquid formulation, a granular formulation to thesoil, a nursery box treatment or a dip of transplants. Of note is acomposition of the present invention in the form of a soil drench liquidformulation. Also of note is a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of the present inventionor with a composition comprising a biologically effective amount of acompound of the present invention. Of further note is this methodwherein the environment is soil and the composition is applied to thesoil as a soil drench formulation. Of further note is that compounds ofthis invention are also effective by localized application to the locusof infestation. Other methods of contact include application of acompound or a composition of the invention by direct and residualsprays, aerial sprays, gels, seed coatings, microencapsulations,systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols,dusts and many others. One embodiment of a method of contact is adimensionally stable fertilizer granule, stick or tablet comprising acompound or composition of the invention. The compounds of thisinvention can also be impregnated into materials for fabricatinginvertebrate control devices (e.g., insect netting).

Compounds of this invention are also useful in seed treatments forprotecting seeds from invertebrate pests. In the context of the presentdisclosure and claims, treating a seed means contacting the seed with abiologically effective amount of a compound of this invention, which istypically formulated as a composition of the invention. This seedtreatment protects the seed from invertebrate soil pests and generallycan also protect roots and other plant parts in contact with the soil ofthe seedling developing from the germinating seed. The seed treatmentmay also provide protection of foliage by translocation of the compoundof this invention or a second active ingredient within the developingplant. Seed treatments can be applied to all types of seeds, includingthose from which plants genetically transformed to express specializedtraits will germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensistoxin or those expressing herbicide resistance such as glyphosateacetyltransferase, which provides resistance to glyphosate.

One method of seed treatment is by spraying or dusting the seed with acompound of the invention (i.e. as a formulated composition) beforesowing the seeds. Compositions formulated for seed treatment generallycomprise a film farmer or adhesive agent. Therefore typically a seedcoating composition of the present invention comprises a biologicallyeffective, amount of a compound of Formula 1, an N-Oxide or saltthereof, and a film former or adhesive agent. Seed can be coated byspraying a flow able suspension concentrate directly into a tumbling bedof seeds and then drying the seeds. Alternatively, other formulationtypes such as wetted powders, solutions, suspoemulsions, emulsifiableconcentrates and emulsions in water can be sprayed on the seed. Thisprocess is particularly useful for applying film coatings on seeds.Various coating machines and processes are available to one skilled inthe art. Suitable processes include those listed in P. Kosters et al.,Seed Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57, andreferences listed therein.

The treated seed typically comprises a compound of the present inventionin an amount from about 0.1 g to 1 kg per 100 kg of seed (i.e. fromabout 0.0001 to 1% by weight of the seed before treatment). A flowablesuspension formulated for seed treatment typically comprises from about0.5 to about 70% of the active ingredient, from about 0.5 to about 30%of a film-forming adhesive, from about 0.5 to about 20% of a dispersingagent, from 0 to about 5% of a thickener, from 0 to about 5% of apigment and/or dye, from 0 to about 2% of an antifoaming agent, from 0to about 1% of a preservative, and from 0 to about 75% of a volatileliquid diluent.

The compounds of this invention can be incorporated into a baitcomposition that is consumed by an invertebrate pest or used within adevice such as a trap, bait station, and the like. Such a baitcomposition can be in the form of granules which comprise (a) activeingredients, namely a biologically effective amount of a compound ofFormula 1, an N-oxide, or salt thereof; (b) one or more food materials;optionally (c) an attractant, and optionally (d) one or more humectants.Of note are granules or bait compositions which comprise between about0.001-5% active ingredients, about 40-99% food material and/orattractant; and optionally about 0.05-10% humectants, which areeffective in controlling soil invertebrate pests at very low applicationrates, particularly at doses of active ingredient that are lethal byingestion rather than by direct contact. Some food materials canfunction both as a food source and an attractant. Food materials includecarbohydrates, proteins and lipids. Examples of food materials arevegetable flour, sugar, starches, animal fat, vegetable oil, yeastextracts and milk solids. Examples of attractants are odorants andflavorants, such as fruit or plant extracts, perfume, or other animal orplant component, pheromones or other agents known to attract a targetinvertebrate pest. Examples of humectants, i.e. moisture retainingagents, are glycols and other polyols, glycerine and sorbitol. Of noteis a bait composition (and a method utilizing such a bait composition)used to control at least one invertebrate pest selected from the groupconsisting of ants, termites and cockroaches. A device for controllingan invertebrate pest can comprise the present bait composition and ahousing adapted to receive the bait composition, wherein the housing hasat least one opening sized to permit the invertebrate pest to passthrough the opening so the invertebrate pest can gain access to the baitcomposition from a location outside the housing, and wherein the housingis further adapted to be placed in or near a locus of potential or knownactivity for the invertebrate pest.

The compounds of this invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of a compound of the presentinvention. Combinations with spray oils, spray oil concentrations,spreader stickers, adjuvants, other solvents, and synergists such aspiperonyl butoxide often enhance compound efficacy. For nonagronomicuses such sprays can be applied from spray containers such as a can, abottle or other container, either by means of a pump or by releasing itfrom a pressurized container, e.g., a pressurized aerosol spray can.Such spray compositions can take various forms, for example, sprays,mists, foams, fumes or fog. Such spray compositions thus can furthercomprise propellants, foaming agents, etc. as the case may be. Of noteis a spray composition comprising a biologically effective amount of acompound or a composition of the present invention and a carrier. Oneembodiment of such a spray composition comprises a biologicallyeffective amount of a compound or a composition of the present inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone invertebrate pest selected from the group consisting of mosquitoes,black flies, stable flies, deer flies, horse flies, wasps, yellowjackets, hornets, ticks, spiders, ants, gnats, and the like, includingindividually or in combinations.

Nonagronomic applications include protecting an animal, particularly avertebrate, more particularly a homeothermic vertebrate (e.g., mammal orbird) and most particularly a mammal, from an invertebrate parasiticpest by administering a parasiticidally effective (i.e. biologicallyeffective) amount of a compound of the invention, typically in the formof a composition formulated for veterinary use, to the animal to beprotected. Therefore of note is a method for protecting an animalcomprising administering to the animal a parasiticidally effectiveamount of a compound of the invention. As referred to in the presentdisclosure and claims, the terms “parasiticidal” and “parasiticidally”refers to observable effects on an invertebrate parasite pest to provideprotection of an animal from the pest. Parasiticidal effects typicallyrelate to diminishing the occurrence or activity of the targetinvertebrate parasitic pest. Such effects on the pest include necrosis,death, retarded growth, diminished mobility or lessened ability toremain on or in the host animal, reduced feeding and inhibition ofreproduction. These effects on invertebrate parasite pests providecontrol (including prevention, reduction or elimination) of parasiticinfestation or infection of the animal. Examples of invertebrateparasitic pests controlled by administering a parasiticidally effectiveamount of a compound of the invention to an animal to be protectedinclude ectoparasites (arthropods, acarines, etc) and endoparasites(helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans,etc.). In particular, the compounds, of this invention are effectiveagainst ectoparasites including: flies such as Haematobia (Lyperosia)irritans (horn fly), Stomoxys calcitrans (stable fly), Simulium spp.(blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly),Musca autumnalis (face fly), Musca domestica (house fly), Morelliasimplex (sweat fly), Tabanus spp. (horse fly), Hypoderma bovis,Hypoderma lineatin, Lucilia sericata, Lucilia cuprina (green blowfly),Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis (nasalbotfly), Culicoides spp. (midges), Hippobosca equine, Gastrophilusinstestinalis, Gastrophilus haemorrhoidalis and Gastrophilus naslis;ices such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinusasini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosusand Trichodectes canis; keds such as Melophagus ovinus; mites such asPsoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi,Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectescyanotis (ear mites); ticks such as Ixodes spp., Boophilus spp.,Rhipicephalus spp., Amblyomma spp., Dermacentor spp., Hyalomma spp. andHaemaphysalis spp.; and fleas such as Ctenocephalides fells (cat flea)and Ctenocephalides canis (dog flea).

Nonagronomic applications in the veterinary sector are by conventionalmeans such as by enteral administration in the form of, for example,tablets, capsules, drinks, drenching preparations, granulates, pastes,boli, feed-through procedures, or suppositories; or by parenteraladministration, such as by injection (including intramuscular;subcutaneous, intravenous, intraperitoneal), implants; by nasaladministration; by topical administration, for example, in the form ofimmersion or dipping, spraying, washing, coating with powder, orapplication to a small area of the animal, and through articles such asneck collars, ear tags, tail bands, limb bands or halters which comprisecompounds or compositions of the present invention.

Typically a parasiticidal composition according to the present inventioncomprises a mixture of a compound of Formula 1, an N-oxide or a saltthereof, with one or more pharmaceutically or veterinarily acceptablecarriers comprising excipients and auxiliaries selected with regard tothe intended route of administration (e.g., oral, topical or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note is a composition for protectingan animal from an invertebrate parasitic pest comprising a parasiticallyeffective amount of a compound of the invention and at least onecarrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, a compound of the present invention can beformulated in suspension, solution or emulsion in oily or aqueousvehicles, and may contain adjuncts such as suspending, stabilizingand/or dispersing agents. Pharmaceutical compositions for injectioninclude aqueous solutions of water-soluble forms of active ingredients(e.g., a salt of an active compound), preferably in physiologicallycompatible buffers containing other excipients or auxiliaries as areknown in the art of pharmaceutical formulation.

For oral administration including solutions (the most readily availableform for absorption), emulsions, suspensions, pastes, gels, capsules,tablets, boluses powders, granules, rumen-retention and feed/water/lickblocks, a compound of the present invention can be formulated withbinders/fillers known in the art to be suitable for oral administrationcompositions, such as sugars (e.g., lactose, sucrose, mannitol,sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potatostarch), cellulose and derivatives (e.g., methylcellulose,carboxymethylcellulose, ethylhydroxycellulose), protein derivativeszein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol,polyvinylpyrrolidone). If desired, lubricants (e.g., magnesiumstearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthangum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates. Such feed concentrate-containingcompositions can, in addition to the parasiticidal active ingredients,comprise additives promoting animal health or growth, improving qualityof meat from animals for slaughter or otherwise useful to animalhusbandry. These additives can include, for example, vitamins,antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostatsand hormones.

Compounds of the present invention have been discovered to havefavorable pharmacokinetic and pharmacodynamic properties providingsystemic availability from oral administration and ingestion. Thereforeafter ingestion by the animal to be protected, parasiticidally effectiveconcentrations of compounds of the invention in the bloodstream protectthe treated animal from blood-sucking pests such as fleas, ticks andlice. Therefore of note is a composition for protecting an animal froman invertebrate parasite pest in a form for oral administration (i.e.comprising, in addition to a parasiticidally effective amount of acompound of the invention, one or more carriers selected from bindersand fillers suitable for oral administration and feed concentratecarriers).

Formulations for topical administration are typically in the form of apowder, cream, suspension, spray, emulsion, foam, paste, aerosol,ointment, salve or gel. More typically a topical formulation is awater-soluble solution, which can be in the form of a concentrate thatis diluted before use. Parasiticidal compositions suitable for topicaladministration typically comprise a compound of the present inventionand one or more topically suitable carriers. In applications of aparasiticidal composition topically to the exterior of an animal as aline or spot (i.e. “spot-on” treatment), the active ingredient isexpected to migrate over the surface of the active to cover most or allof its external surface area. As a result, the treated animal isparticularly protected from invertebrate pests that feed off theepidermis of the animal such as ticks, fleas and lice. Thereforeformulations for topical localized administration often comprise atleast one organic solvent to facilitate transport of the activeingredient over the skin and/or penetration into the epidermis of theanimal. Solvents commonly used as carriers in such formulations includepropylene glycol, paraffins, aromatics, esters such as isopropylmyristate, glycol ethers, and alcohols Such as ethanol and n-propanol.

The rate of application required for effective control (i.e.“biologically effective amount”) will depend on such factors as thespecies of invertebrate to be controlled, the pest's life cycle, lifestage, its size, location, time of year, host crop or animal, feedingbehavior, mating behavior, ambient moisture, temperature, and the like.Under normal circumstances, application rates of about 0.01 to 2 kg ofactive ingredients per hectare are sufficient to control pests inagronomic ecosystems, but as little as 0.0001 kg/hectare may besufficient or as much as 8 kg/hectare may be required. For nonagronomicapplications, effective use rates will range from about 1.0 to 50mg/square meter but as little as 0.1 mg/square meter may be sufficientor as much as 150 mg/square meter may be required. One skilled in theart can easily determine the biologically effective amount necessary forthe desired level of invertebrate pest control.

In general for veterinary use, a compound of Formula 1, an N-oxide or asalt thereof, is administered in a parasiticidally effective amount toan animal to be protected from invertebrate parasite pests. Aparasiticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target invertebrate parasite pest. One skilled in theart will appreciate that the parasitically effective dose can vary forthe various compounds and compositions of the present invention, thedesired parasitical effect and duration, the target invertebrate pestspecies, the animal to be protected, the mode of application and thelike, and the amount needed to achieve a particular result can bedetermined through simple experimentation.

For oral administration to homeothermic animals, the daily dosage of acompound of the present invention typically ranges from about 0.01 mg/kgto about 100 mg/kg, more typically from about 0.5 mg/kg to about 100mg/kg, of animal body weight. For topical (e.g., denial) administration,dips and sprays typically contain from about 0.5 ppm to about 5000 ppm,more typically from about 1 ppm to about 3000 ppm, of a compound of thepresent invention.

The following abbreviations are used in the Index Tables A-D whichfollow: t is tertiary, s is secondary, n is normal, i is iso, c iscyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, Bu isbutyl, c-Pr is cyclopropyl, t-Bu is tert-butyl, Ph is phenyl, OMe ismethoxy, CF₃ means trifluoromethyl, —CN is cyano and —NO₂ is nitro. Theabbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared. In Index Tables A,B and C, (R²)_(k) refers to the combination of (R²)_(n) as shown withinstances of CR² for B¹, B² and B³, and thus k is 1, 2, 3, 4 or 5 forIndex Tables A, B and C.

INDEX TABLE A

Compound R¹ (R²)_(k) A¹ A² A³ Q m.p. (°C) 1 (Ex. 1) CF₃ 3-Cl, 5-Cl CH CHCH 1H-pyrazol-1-yl  174-175* 2 (Ex. 2) CF₃ 3-Cl, 5-Cl CH C—Me CH1H-pyrazol-1-yl * 3 (Ex. 3) CF₃ 3-Cl, 5-Cl CH CH CH 2-pyridinyl *  4 CF₃3-Cl, 5-Cl CH CH CH 5-CF₃-1H-imidazol-2-yl  135-136*  5 CF₃ 3-Cl, 5-ClCH CH CH 1H-imidazol-2-yl 175-176  6 CF₃ 3-Cl, 5-Cl CH CH CH4-(1,1-dimethylethyl)-2-thiazolyl *  7 CF₃ 3-Cl, 5-Cl CH CH CH1,2,3-thiadiazol-4-yl 178-179  8 CF₃ 3-Cl, 5-Cl CH C—Me CH3-(CF₃)-1H-pyrazol-1-yl *  9 CF₃ 3-Cl, 5-Cl CH CH CH1H-1,2,4-triazol-1-yl 181-182 10 CF₃ 3-Cl, 5-Cl CH CH CH 2-thienyl189-190 11 CF₃ 3-Cl, 5-Cl CH CH CH 4-Br-3-Me-1H-pyrazol-1-yl 129-131 12CF₃ 3-Cl, 5-Cl CH CH CH 3-(4-pyridinyl)-1H-pyrazol-1-yl * 13 CF₃ 3-Cl,5-Cl CH CH CH 4-iodo-1H-pyrazol-1-yl 174-175 14 CF₃ 3-Cl, 5-Cl CH C—MeCH 1H-1,2,4-triazol-1-yl 126-127 15 CF₃ 3-Cl, 5-Cl CH CH CH(4-Cl—Ph)-1H-pyrazol-1-yl 214-215 16 CF₃ 3-Cl, 5-Cl CH C—F CH1H-1,2,4-triazol-1-yl 135-137 17 CF₃ 3-Cl, 5-Cl CH C—F CH1H-pyrazol-1-yl 115-123 18 CF₃ 3-Cl, 5-Cl CH C—Me CH1H-1,2,3-triazol-1-yl * 19 CF₃ 3-Cl, 5-Cl CH CH CH 1H-1,2,3-triazol-1-yl131-132 20 CF₃ 3-Cl, 5-Cl CH CH CH 3-(CF₃)-1H-1,2,4-triazol-1-yl * 21CF₃ H CH CH CH 1H-1,2,4-triazol-1-yl 133-134 22 CF₃ 3-Cl, 4-Cl CH CH CH1H-1,2,4-triazol-1-yl 166-167 23 CF₃ 3-Cl CH CH CH 1H-1,2,4-triazol-1-yl142-143 24 CF₃ 3-CF₃, 5-CF₃ CH CH CH 1H-1,2,4-triazol-1-yl 116-117 25CF₃ 3-F, 5-F CH CH CH 1H-1,2,4-triazol-1-yl 164-165 26 CF₃ 3-Br, 5-Br CHCH CH 1H-1,2,4-triazol-1-yl 165-166 27 CF₃ 2-Cl CH CH CH1H-1,2,4-triazol-1-yl 178-179 28 CF₃ 3-Cl, 6-F CH CH CH1H-1,2,4-triazol-1-yl * 29 CF₃ 3-Cl, 5-Cl CH CH CH 1H-pyrrol-1-yl202-203 30 CF₃ 3-Cl, 5-Cl C—Cl CH CH 1H-1,2,4-triazol-1-yl 141-143 31CF₃ 3-Cl, 5-Cl CH C—CF₃ CH 1H-1,2,4-triazol-1-yl * 32 CF₃ 3-Cl, 4-F CHCH CH 1H-1,2,4-triazol-1-yl 170-171 33 CF₃ 3-Cl, 5-Cl CH CH CH4-morpholinyl 139-140 34 Et 3-Cl, 5-Cl CH CH CH 1H-1,2,4-triazol-1-yl134-135 35 Me 3-Cl, 5-Cl CH CH CH 1H-1,2,4-triazol-1-yl 151-152 36 CF₃3-Cl, 5-Cl CH C—Cl CH 1H-1,2,4-triazol-1-yl * 37 CF₃ 3-Cl, 5-Cl CH C—ClCH 1H-1,2,3-triazol-1-yl 164-165 38 CF₃ 3-Cl, 5-Cl CH C—NO₂ CH1H-1,2,4-triazol-1-yl 61-62 39 CF₃ 3-Cl, 5-Cl C—Cl CH CH 1H-pyrazol-1-yl116-118 40 CF₃ 3-Cl, 5-Cl CH C—NO₂ CH 1H-pyrazol-1-yl 141-142 41 CF₃3-Cl, 5-Cl CH CH CH 4-(2-pyridinyl)-1-piperazinyl 178-179 42 CF₃ 3-Cl,5-Cl CH C—CN CH 1H-1,2,4-triazol-1-yl 64-66  43** CF₃ 3-Cl, 5-Cl CH CHCH 1H-1,2,4-triazol-1-yl *  44** CF₃ 3-Cl, 5-Cl CH CH CH1H-1,2,4-triazol-1-yl * 45 CF₃ 3-Me, 5-Me CH CH CH 1H-1,2,4-triazol-1-yl156-157 46 CF₃ 3-Br, 5-Me CH CH CH 1H-1,2,4-triazol-1-yl 187-188 47 CF₃3-Br, 5-F CH CH CH 1H-1,2,4-triazol-1-yl 144-145 48 CF₃ 3-Br, 5-OMe CHCH CH 1H-1,2,4-triazol-1-yl 130-131 49 —CN 3-Cl, 4-Cl CH CH CH1H-1,2,4-triazol-1-yl * 50 CF₃ 3-CN CH CH CH 1H-1,2,4-triazol-1-yl186-187 51 CF₃ 3-CN, 5-Me CH CH CH 1H-1,2,4-triazol-1-yl 234-235 52 CF₃3-CN, 5-CN CH CH CH 1H-1,2,4-triazol-1-yl 223-224 53 CF₃ 3-CN, 4-F CH CHCH 1H-1,2,4-triazol-1-yl 188-189 54 CF₃ 2-Cl, 3-Cl CH CH CH1H-1,2,4-triazol-1-yl 170-171 55 CF₃ 3-OMe, 4-OMe CH CH CH1H-1,2,4-triazol-1-yl 169-170 56 CF₃ 3-Br, 2-F CH CH CH1H-1,2,4-triazol-1-yl 167-168 57 CF₃ 3-Cl, 5-Cl CH C—CN CH1H-pyrazol-1-yl 164-165 58 CF₃ 3-Cl, 5-Cl CH C—NH₂ CH1H-1,2,4-triazol-1-yl 240-241 59 CF₃ 3-Cl, 5-Cl CH C—NHCOCH₃ CH1H-1,2,4-triazol-1-yl 221-222 60 CF₃ 3-Cl, 5-Cl CH C—NHCO₂CH₃ CH1H-1,2,4-triazol-1-yl 91-92 61 CF₃ 3-Cl, 5-Cl CH C—CN CH1H-imidazol-1-yl 150-153 62 CF₃ 3-Cl, 5-Cl CH C—OMe CH1H-1,2,4-triazol-1-yl 179-180 63 CF₃ 3-Cl, 5-Cl CH C—Br CH1H-1,2,4-triazol-1-yl 72-73 64 CF₃ 3-Cl, 5-Cl CH C—CONH₂ CH1H-1,2,4-triazol-1-yl * 65 CF₃ 3-Cl, 5-Cl CH C—CSNH₂ CH1H-1,2,4-triazol-1-yl 139-140 66 CF₃ 3-Cl, 5-Cl CH C—CN CH5-(Me)-1H-1,2,4-triazol-1-yl * 67 CF₃ 3-Cl, 5-Cl CH C—CN CH3-(CO₂Me)-1H-1,2,4-triazol-1-yl 102-103 68 CF₃ 3-Cl, 5-Cl CH C—CN CH3-(CN)-1H-1,2,4-triazol-1-yl 80-81 69 CF₃ 3-Cl, 5-Cl CH C—CN CH3-(NH₂)-1H-1,2,4-triazol-1-yl 102-103 70 CF₃ 3-Cl, 5-Cl CH C—CN CH3-(Br)-1H-1,2,4-triazol-1-yl 84-85 71 CF₃ 3-Cl, 5-Cl CH C—CN CH2H-tetrazol-2-yl 143-153 72 CF₃ 3-Cl, 5-Cl CH C—CN CH 1H-tetrazol-1-yl84-85 73 CF₃ 3-Cl, 5-Cl CH C—CN CH 3-(4-pyridinyl)-1H-pyrazol-1-yl203-204 74 CF₃ 3-Cl, 5-Cl CH C—CO₂CH₃ CH 1H-1,2,4-triazol-1-yl * 75 CF₃3-Cl, 5-Cl CH C—Br CH 5-(NH₂)-1H-1,2,4-triazol-1-yl * 76 CF₃ 3-Cl, 5-ClCH C—I CH 1H-1,2,4-triazol-1-yl * 77 CF₃ 3-Cl, 5-Cl CH C—CN CH3-(2-pyridinyl)-1H-1,2,4-triazol-1-yl 90-91 78 CF₃ 3-Cl, 5-Cl CH C—Br CH3-(2-pyridinyl)-1H-1,2,4-triazol-1-yl 71-72 79 CF₃ 3-Cl, 5-Cl CH CH CH5-(Br)-1H-1,2,4-triazol-1-yl * 80 CF₃ 3-Cl, 5-Cl CH CH CH4H-1,2,4-triazol-4-yl >250 81 CF₃ 3-Cl, 5-Cl CH CH N1H-1,2,4-triazol-1-yl 160-162 82 CF₃ 3-Cl, 5-Cl CH C—Cl N1H-1,2,4-triazol-1-yl 144-145 83 CF₃ 3-Cl, 5-Cl CH CH CH3-(CF₃)-1H-pyrazol-1-yl 110-112 84 CF₃ 3-Cl, 5-Cl CH C—Me CH5-(2-pyridinyl)-1H-1,2,4-triazol-3-yl 232-233 85 CF₃ 3-Cl, 5-Cl CH CH CH4-(2-pyridinyl)-2-thiazolyl 198-199 86 CF₃ 3-Cl, 5-Cl CH CH CH5-pyrimidinyl * 87 CF₃ 3-Cl, 5-Cl CH CH CH 2-pyrazinyl * 88 CF₃ 3-Cl,5-Cl CH CH CH 3-pyridinyl * 89 CF₃ 3-Br, 5-Br CH C—CN CH1H-1,2,4-triazol-1-yl * *See Index Table E for ¹H NMR data. **Compounds43 and 44 are enantiomeric isomers separated by chiral columnchromatography, though the absolute configuration of each compound hasnot been determined yet.

INDEX TABLE B

Com- pound (R²)_(k) A¹ A² A³ R²¹ R²² m.p. (°C) 101 H CH C—Me CH H i-Pr *102 3-Cl, 5-Cl CH C—Me CH H i-Pr * 103 3-Cl, 5-Cl CH C—Me CH H CH₂CF₃ *104 H CH C—Me CH H CH₂CF₃ * 105 3-Cl, 5-Cl CH C—Me CH H CH(CH₃)CH₂CH₃ *106 3-Cl, 4-Cl CH C—Me CH H CH(CH₃)CH₂CH₃ * 107 3-Cl, 5-Cl CH C—Me CH HCH₂—c-Pr 105-106 108 3-Cl, 5-Cl CH C—Me CH Me Me 142-143 109 3-Cl, 5-ClCH C—Me CH H CH₂CN 64-65 110 3-Cl, 5-Cl CH C—Me CH Me CH₂Ph * 111 3-Cl,5-Cl CH C—Me CH H Me 140-142 112 3-Cl, 5-Cl CH C—Me CH H C(CH₃)₂CH₂SCH₃88-89 113 3-Cl, 5-Cl CH C—Me CH H CH₂-2-pyridinyl 57-58 (Ex. 4) 1143-Cl, 5-Cl CH CH CH H CH₂-2-pyridinyl * 115 3-Cl, 5-Cl CH CH CH H i-Pr133-134 116 3-Cl, 5-Cl CH CH CH H CH₂CN 113-114 117 3-Cl, 5-Cl CH CH CHH CH₂CF₃ 154-155 118 3-Cl, 5-Cl CH CH CH H Me 58-59 119 3-Cl, 5-Cl CHC—Me CH H H 129-130 120 3-Cl, 5-Cl CH C—Me CH H CH₂C≡CH * 121 3-Cl, 5-ClCH C—Me CH H CH₂C═CH₂ 73-74 122 3-Cl, 5-Cl CH C—Me CH H n-Pr 101-102 1233-Cl, 5-Cl CH C—Me CH H Et 105-106 124 3-Cl, 5-Cl CH CH N Me Me 137-138125 3-Cl, 5-Cl CH C—CN CH Me Me 197-198 *See Index Table E for ¹H NMRdata.

INDEX TABLE C

Compound (R²)_(k) A¹ A² A³ R²⁵ p m.p. (°C) 201 H CH CH CH Me 2 164-166202 3-Cl, 5-Cl CH CH CH CH₂—Ph 0 108-109 203 3-Cl, 5-Cl CH C—NO₂ CHCH₂—Ph 0 106-108 204 3-Cl, 5-Cl CH CH N CH₂—Ph 0 110-111 205 3-Cl, 5-ClCH C—Br CH Me 0 * 206 (Ex. 5) 3-Cl, 5-Cl CH C—CN CH Me 0 ** 207 3-Cl,5-Cl CH C—CN CH Me 1 * 208 (Ex. 6) 3-Cl, 5-Cl CH C—CN CH Me 2 ** 209(Ex. 7) 3-Cl, 5-Cl CH CH CH Me 2 ** 210 3-Cl, 5-Cl CH C—CN CH Et 0 * 2113-Cl, 5-Cl CH C—CN CH Et 2 * 212 3-Cl, 5-Cl CH C—Br CH Me 2 * 213 3-Cl,5-Cl CH C—Me CH Me 2 * 214 3-Cl, 5-Cl CH C—CN CH CH₂CF₃ 2 * *See IndexTable E for ¹H NMR data. **See the specific Example for ¹H NMR data.

INDEX TABLE D

Com- m.p. pound B¹ B² B³ (R²)_(n) A¹ A² A³ Q (°C) 301 C—Cl N CH H CH2-CN CH 1H-1,2,4- 181-182 triazol-1-yl

INDEX TABLE E Compd. No. ¹H NMR Data (CDCl₃ solution unless indicatedotherwise)^(a) 1 (DMSO-d₆) δ 8.63 (d, 1H), 8.00 (d, 2H) 7.84 (m, 4H),7.64 (d, 2H), 6.60 (m, 1H), 4.38 (AB quartet, 2H). 2 δ 7.75 (d, 1H),7.64 (d, 2H), 7.58 (dd, 1H), 7.52 (d, 2H), 7.43 (m, 2H), 6.48 (t, 1H),4.11 (d, 1H), 3.73 (d, 1H), 2.34 (s, 3H). 3 δ 8.8 (m, 1H), 8.05 (m, 2H),7.8 (m, 3H), 7.76 (d, 2H), 7.2 (d, 2H), 4.2 (d, 1H), 3.8(d, 1H). 6 δ8.01 (d, 2H), 7.64 (d, 2H), 7.70 (d, 2H), 7.53 (s, 2H), 7.43 (s, 1H),6.95 (s, 1H), 4.11 (d, 1H), 3.72 (d, 1H), 1.40 (s, 9H). 8 δ 7.65 (m,2H), 7.58 (d, 2H), 7.50 (s, 2H), 7.41 (s, 1H), 7.40 (m, 1H), 6.72 (s,1H), 3.70 (d, 1H), 2.29 (s, 3H). 12 δ 8.35 (d, 1H), 8.22-8.19 (m, 1H),8.07 (s, 1H), 7.87 (d, 2H), 7.80-7.78 (m, 4H), 7.54 (s, 2H), 7.44 (s,1H), 6.91 (s, 1H), 4.13 (d, 1H), 3.74 (d, 1H). 18 δ 7.84 (s, 2H), 7.77(d, 1H), 7.64 (s, 1H), 7.59 (d, 1H), 7.50 (m, 2H), 7.41 (s, 1H), 7.23(s, 1H), 4.10 (d, 1H), 3.71 (d, 1H), 2.46 (s, 3H). 20 δ 8.44 (s, 1H),8.17 (s, 1H), 7.60 (d, 2H), 7.50 (s, 2H), 7.42 (s, 1H), 6.64 (d, 2H),4.05 (d, 1H), 3.66 (d, 1H). 28 δ 8.12-8.09 (m, 3H), 7.59-7.56 (m, 5H),7.44 (s, 1H), 4.21 (d, 1H), 3.83 (d, 1H). 31 δ 8.37 (s, 1H), 8.17 (s,1H), 8.10 (s, 1H), 8.04 (d, 1H), 7.66 (d, 1H), 7.52 (d, 1H), 7.45 (s,1H), 4.17 (d, 1H), 3.71 (d, 1H). 36 δ 8.66 (s, 1H), 8.16 (s, 1H), 7.89(s, 1H), 7.73 (s, 1H), 7.51 (s, 2H), 7.48 (d, 1H), 4.10 (d, 1H), 3.73(d, 1H). 43 δ 8.69 (s, 1H), 8.16 (s, 1H), 7.81-7.78 (m, 4H), 7.52 (s,2H), 7.44 (s, 1H), 4.12 (d, 1H), 3.74 (d, 1H). 44 δ 8.66 (s, 1H), 8.14(s, 1H), 7.81-7.78 (m, 4H), 7.53 (s, 2H), 7.44 (s, 1H), 4.13 (d, 1H),3.74 (d, 1H). 49 δ 8.686 (s, 1H), 7.86-7.70 (m, 6H), 7.58 (s, 1H), 7.50(s, 1H), 4.28 (d, 1H), 3.79 (d, 1H). 64 δ 8.47 (s, 1H), 8.16 (s, 1H),8.02 (s, 1H), 7.98 (d, 1H), 7.57 (d, 1H), 7.51 (s, 2H), 7.45 (s, 1H),6.05 (br s, NH), 5.63 (br s, NH), 4.13 (d, 1H), 3.76 (d, 1H). 66 δ8.01-8.09 (m, 3H), 7.61 (d, 1H), 7.51 (s, 2H), 7.46 (s, 1H), 4.12 (d,1H), 3.75 (d, 1H), 2.53 (s, 3H). 74 δ 8.39 (s, 1H), 8.14 (s, 1H), 8.12(s, 1H), 8.04 (d, 1H), 7.60 (d, 1H), 7.52 (s, 2H), 7.45 (s, 1H), 4.14(d, 1H), 3.77 (s, 3H), 3.76 (d, 1H). 75 δ 8.29 (s, 1H), 7.97 (s, 1H),7.70 (d, 1H), 7.60 (d, 1H), 7.48 (s, 2H), 7.41 (s, 1H), 4.26 (br s,NH₂), 4.05 (d, 1H), 3.78 (d, 1H). 76 δ 8.47 (s, 1H), 8.26 (s, 1H), 8.16(s, 1H), 7.82 (d, 1H), 7.51 (s, 2H), 7.50 (d, 1H), 7.45 (s, 1H), 4.10(d, 1H), 3.72 (d, 1H). 79 δ 8.30 (d, 2H), 7.85 (d, 2H), 7.74 (m, 1H),7.51 (s, 2H), 7.45 (s, 1H), 4.11 (d, 1H), 3.73 (d, 1H). 86 δ 9.25 (s,1H), 8.98 (s, 2H), 7.84 (m, 2H), 7.66 (m, 2H), 7.53 (s, 2H), 7.43 (s,1H), 4.13 (d, 1H), 3.75 (d, 1H). 87 (Acetone-d₆) δ 9.26 (s, 1H), 8.72(s, 1H), 8.62 (s, 1H), 8.29 (m, 2H), 7.96 (m, 2H), 7.70 (s, 2H), 7.65(s, 1H), 4.48 (d, 1H), 4.33 (d, 1H). 88 δ 8.87 (m, 1H), 8.64 (m, 1H),7.90 (m, 1H), 7.78 (m, 2H), 7.66 (m, 2H), 7.53 (s, 2H), 7.44 (s, 1H),7.42 (m, 1H), 4.13 (d, 1H), 3.74 (d, 1H). 89 δ 8.89 (s, 1H), 8.22 (s,1H), 8.11 (s, 1H), 8.09 (d, 1H), 7.93 (d, 1H), 7.77 (s, 1H), 7.70 (s,2H), 4.14 (d, 1H), 3.77 (d, 1H). 101 δ 8.11 (d, 1H), 7.68 (s, 1H), 7.6(m, 3H), 7.44 (m, 3H), 3.77 (d, 1H), 2.65 (s, 3H), 2.63 (m, 1H), 1.32(d, 6H). 102 δ 8.06 (d, 1H), 7.65 (s, 1H), 7.58 (d, 1H), 7.51 (s, 2H),7.44 (s, 1H), 4.39 (d, 1H), 4.10, (d, 1H), 3.72, (d, 1H), 2.674 (s, 3H),2.67 (m, 1H), 1.1 (d, 6H). 103 δ 8.04 (d, 1H), 7.67 (s, 1H), 7.58 (d,1H), 7.50 (s, 2H), 7.44 (s, 1H), 4.97 (t, 1H), 4.1 (d, 1H), 3.71 (m,3H), 2.68 (s, 3H). 104 δ 8.02 (d, 1H), 7.69 (s, 1H), 7.6 (m, 3H), 7.4(m, 3H), 4.94 (t, 1H), 4.1 (d, 1H), 3.79 (d, 1H), 3.7 (m, 1H), 2.68 (s,3H). 105 δ 8.13 (d, 1H), 7.68 (s, 1H), 7.64 (d, 1H), 7.5 (s, 2H), 7.44(s, 1H), 4.1 (d, 1H), 3.72 (d, 1H), 3.25 (d, 2H), 2.73 (s, 3H), 2.1 (m,1H), 0.98 (m, 6H). 106 δ 8.11 (d, 1H), 7.72 (d, 1H), 7.68 (s, 1H), 7.65(d, 1H), 7.53 (d, 1H), 7.46 (d, 1H), 4.1 (d, 1H), 3.7 (d, 1H), 3.24 (d,2H), 2.72 (s, 3H), 2.13 (m, 1H), 0.98 (m, 6H). 110 δ 7.99 (d, 1H), 7.67(s, 1H), 7.6 (d, 1H), 7.52 (s, 2H), 7.44 (s, 1H), 7.3-7.4 (m, 4H), 7.24(s, 1H), 4.316 (s, 1H), 4.1 (d, 1H), 3.72 (d, 1H), 2.70 (s, 3H), 2.69(s, 3H). 114 δ 8.44 (d, 1H), 7.92, (d, 2H), 7.74 (d, 1H), 7.6 (t, 1H),7.5 (s, 2H), 7.44 (s, 1H), 7.15 (d, 2H), 6.13 (br s, 1H), 4.27 (d, 2H),4.07 (d, 1H), 3.69 (d, 1H). 120 δ 8.05 (d, 1H), 7.67 (s, 1H), 7.57 (d,1H), 7.51 (s, 2H), 7.44 (s, 1H), 4.73 (t, 1H), 4.1 (d, 1H), 3.85 (d,2H), 3.75 (d, 1H), 2.7 (s, 3H), 2.09 (s, 1H). 205 δ 7.78 (s, 1H), 7.6(m, 1H), 7.5 (s, 2H), 7.4 (s, 1H), 7.15 (m, 1H), 4.05 (d, 1H), 3.62 (d,1H), 2.5 (s, 3H). 207 δ 8.2 (m, 1H), 8.1 (m, 1H), 8.08 (m, 1H), 7.5 (s,2H), 7.45 (s, 1H), 4.1 (d, 1H), 3.75 (d, 1H), 2.9 (s, 3H). 210 δ 7.85(m, 1H), 7.8 (s, 1H), 7.5 (s, 2H), 7.42 (s, 1H), 7.39 (m, 1H), 4.04 (d,1H), 3.66 (d, 1H), 3.1 (q, 2H), 1.4 (t, 3H). 211 δ 8.22 (m, 1H), 8.2 (s,1H), 8.06 (m, 1H), 7.5 (s, 2H), 7.46 (s, 1H), 4.12 (d, 1H), 3.78 (d, 1H,3.4 (q, 2H), 1.33 (t, 3H). 212 (Acetone-d₆) δ 8.22 (m, 1H), 8.21 (s,1H), 8.05 (m, 1H), 7.67 (s, 2H), 7.66 (s, 1H), 4.53 (d, 1H), 4.38 (d,1H), 3.36 (s, 3H). 213 (Acetone-d₆) δ 8.06 (m, 1H), 7.85 (s, 1H), 7.83(m, 1H), 7.67 (s, 2H), 7.65 (m, 1H), 4.48 (d, 1H), 4.15 (d, 1H), 3.19(s, 3H), 2.76 (s, 3H). 214 δ 8.3 (m, 1H), 8.25 (s, 1H), 8.1 (m, 1H), 7.5(s, 2H), 7.45 (s, 1H), 4.26 (q, 2H), 4.12 (d, 1H), 3.87 (d, 1H). ^(a1)HNMR data are in ppm downfield from tetramethylsilane. Couplings aredesignated by (s)—singlet, (d)—doublet, (t)—triplet, (q)—quartet,(m)—multiplet, (dd)—doublet of doublets, (br s)—broad singlet.

BIOLOGICAL EXAMPLES OF THE INVENTION

The following Tests demonstrate the control efficacy of compounds ofthis invention on specific pests. “Control efficacy” representsinhibition of invertebrate pest development (including mortality) thatcauses significantly reduced feeding. The pest control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-D for compound descriptions.

Test A

For evaluating control of diamondback moth (Plutella xylostella) thetest unit consisted of a small open container with a 12-14-day-oldradish plant inside. This was pre-infested with 10-15 neonate larvae ona piece of insect diet by use of a core sampler to remove a plug from asheet of hardened insect diet having many larvae growing on it andtransfer the plug containing larvae and diet to the test unit. Thelarvae moved onto the test plant as the diet plug dried out.

Test compounds were formulated using a solution containing 10% acetone,90% water and 300 ppm X-77™ Spreader Lo-Foam Formula non-ionicsurfactant containing alkylarylpolyoxyethylene, free fatty acids,glycols and isopropanol (Loveland Industries, Inc. Greeley, Colo., USA).The formulated compounds were applied in 1 mL of liquid through a SUJ2atomizer nozzle with ⅛ JJ custom body (Spraying Systems Co. Wheaton,Ill., USA) positioned 1.27 cm (0.5 inches) above the top of each testunit. All experimental compounds in these tests were sprayed at 250 ppmreplicated three times. After spraying of the formulated test compound,each test unit was allowed to dry for 1 hour and then a black, screenedcap was placed on top. The test units were held for 6 days in a growthchamber at 25° C. and 70% relative humidity. The level of controlefficacy of the test compound was then visually assessed based on thefoliage feeding damage and the larval mortality of each test unit.

Of the compounds of Formula 1 tested the following provided very good toexcellent levels of control efficacy (20% or less feeding damage or 80%or more mortality): 1, 2, 3, 5, 9, 14, 16, 17, 18, 19, 21, 22, 23, 24,25, 26, 27, 28, 30, 32, 34, 35, 36, 37, 38, 40, 42, 45, 46, 47, 48, 50,52, 53, 56, 57, 59, 60, 61, 62, 63, 64, 65, 66, 68, 69, 70, 71, 72, 75,76, 79, 80, 81, 82, 84, 86, 87, 89, 102, 103, 105, 107, 108, 109, 111,112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122; 123, 205, 206,207, 208, 209, 210, 211, 212, 213 and 301.

Test B

For evaluating control of fall armyworm (Spodoptera frugiperda) the testunit consisted of a small open container with a 4-5-day-old corn (maize)plant inside. This was pre-infested (using a core sampler) with 10-151-day-old larvae on a piece of insect diet.

Test compounds 1, 2 and 3 were formulated and sprayed at 250 ppm asdescribed for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

Of the compounds of Formula 1 tested, the following provided excellentlevels of control efficacy (20% or less feeding damage or 80% or moremortality): 1, 2, 5, 9, 11, 14, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26,27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 40, 42, 43, 44, 45, 46,47; 48, 50, 52, 53, 56, 57, 58, 59, 60, 61, 62, 63, 65, 66, 68, 69, 70,71, 72, 74, 75, 76, 79, 80, 81, 82, 86, 89, 105, 107, 108, 110, 111,112, 113, 115, 117, 118, 119, 120, 121, 122, 123, 202, 205, 206, 207,208, 209, 210, 211, 212 and 213.

Test C

For evaluating control of green peach aphid (Myzus persicae) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 12-15-day-old radish plant inside. This waspre-infested by placing on a leaf of the test plant 30-40 aphids on apiece of leaf excised from a culture plant (cut-leaf method). The larvaemoved onto the test plant as the leaf piece desiccated. Afterpre-infestation, the soil of the test unit was covered with a layer ofsand.

All test compounds were formulated and sprayed at 250 ppm as describedfor Test A and replicated three times. After spraying of the formulatedtest compound, each test unit was allowed to dry for 1 hour and then ablack, screened cap was placed on top. The test units were held for 6days in a growth chamber at 19-21° C. and 50-70% relative humidity. Eachtest unit was then visually assessed for insect mortality.

Of the compounds of Formula 1 tested, the following resulted in 80% ormore mortality: 2, 9, 14, 17, 31, 36, 38, 42, 61, 63, 65, 69, 72, 75, 76and 89.

Test D

For evaluating control of potato leafhopper (Empoasca fabae Harris)through contact and/or systemic means, the test unit consisted of asmall open container with a 5-6-day-old Longio bean plant (primaryleaves emerged) inside. White sand was added to the top of the soil andone of the primary leaves was excised prior to application. Testcompounds were formulated and sprayed at 250 ppm and replicated threetimes as described for Test A. After spraying, the test units wereallowed to dry for 1 hour before they were post-infested with 5 potatoleafhoppers (18 to 21 day old adults). A black, screened cap was placedon the top of the cylinder. The test units were held for 6 days in agrowth chamber at 19-21° C. and 50-70% relative humidity. Each test unitwas then visually assessed for insect mortality.

Of the compounds of Formula 1 tested, the following resulted in 80% ormore mortality: 9, 14, 16, 18, 19, 22, 24, 26, 31, 32, 36, 37, 38, 42,47, 60, 63, 65, 69, 70, 71, 72, 76, 79, 81, 82, 89, 107, 108, 111, 207and 212.

Test E

For evaluating control of cotton melon aphid (Aphis gossypii) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 6-7-day-old cotton plant inside. This was pre-infestedwith 30-40 insects on a piece of leaf according to the cut-leaf methoddescribed for Test C, and the soil of the test unit was covered with alayer of sand. Test compounds were formulated and sprayed at 250 ppm asdescribed for Test A. The applications were replicated three times.After spraying of the formulated test compound, each test unit wasallowed to dry for 1 hour and then a black, screened cap was placed ontop. The test units were held for 6 days in a growth chamber at 19-21°C. and 50-70% relative humidity. Each test unit was then visuallyassessed for insect mortality.

Of the compounds of Formula 1 tested, the following resulted in 80% ormore mortality: 2, 9, 14, 19, 26, 32, 35, 38, 42, 69, 76 and 89.

Test F

For evaluating control of the Western Flower Thrips (Frankliniellaoccidentalis) through contact and/or systemic means, the test unitconsisted of a small Open container with a 5-7-day-old Longio Bean plantinside.

Test compounds were formulated and sprayed at 250 ppm and replicatedthree times as described for Test A. After spraying, the test units wereallowed to dry for 1 hour, then 22-27 adult thrips were added to theunit and then a black, screened cap was placed on top. The test unitswere held for 7 days at 25° C. and 45-55% relative humidity. Each testunit was then visually assessed for insect mortality.

Of the compounds of Formula 1 tested, the following resulted in 80% ormore mortality: 9, 14, 16, 17, 19, 22, 24, 26, 31, 32, 36, 37, 38, 42,47, 63, 65, 69, 70, 72, 74, 76, 79, 81, 82, 89, 205, 209, 212 and 301.

Test G

For evaluating control of silverleaf whitefly (Bemisia tabaci), the testunit consisted of a 14-21-day-old cotton plant grown in Redi-earth®media (Scotts Co.) with at least two true leaves infested with 2nd and3rd instar nymphs on the underside of the leaves.

Test compounds were formulated in no more than 2 mL of acetone and thendiluted with water to 25-30 mL. The formulated compounds were appliedusing a flat fan air-assisted nozzle (Spraying Systems 122440) at 10 psi(69 kPa). Plants were sprayed to run-off on a turntable sprayer. Allexperimental compounds in this screen were sprayed at 250 ppm andreplicated three times. After spraying of the test compound, the testunits were held for 6 days in a growth chamber at 50-60% relativehumidity and 28° C. daytime and 24° C. nighttime temperature. Then theleaves were removed and then dead and live nymphs were counted tocalculate percent mortality.

Of the compounds of Formula 1 tested, the following provided very goodto excellent levels of control efficacy (80% or more mortality): 9, 14,42, 63 and 76.

Test H

For evaluating control of the cat flea (Ctenocephalides felis Bouche), aCD-1® mouse (about 30 g, male, obtained from Charles River Laboratories,Wilmington, Mass.) was orally dosed with a test compound in an amount of10 mg/kg solubilized in propylene glycol/glycerol formal (60:40). Twohours after oral administration of the test compound, approximately 8 to16 adult fleas were applied to each mouse. The fleas were then evaluatedfor mortality 48 hours after flea application to the mouse.

Of the compounds tested, the following compounds caused 20% or moremortality: 42*, 65*, 69* and 205. * means the compound caused 50% ormore mortality.

1. A compound of Formula 1, an N-oxide, or a salt thereof,

wherein: A¹, A² and A³ are independently selected from the groupconsisting of CR³ and N; B¹, B² and B³ are independently selected fromthe group consisting of CR² and N; R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl,C₃-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R⁶; each R² is independently H,halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN or —NO₂; eachR³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₃-C₆ haloalkenyl, C₂-C₆ alkynyl, C₃-C₆ haloalkynyl, C₃-C₆cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,—N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —C(W)OR⁵, —CN or —NO₂; Q is a phenyl ring or a5- or 6-membered saturated or unsaturated heterocyclic ring, each ringoptionally, substituted with one or more substituents independentlyselected from halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, —CN, —NO₂, —N(R⁴)R⁵,—C(W)N(R⁴)R⁵, —C(O)OR⁵ and R⁸; or —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or—S(O)(═NR²⁸)R²⁹; each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl; each R⁵ isindependently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R⁷; each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆alkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CNor —NO₂; each R⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN, —NO₂ orQ¹; each R⁸ is independently a phenyl ring or a pyridinyl ring, eachring optionally substituted with one or more substituents independentlyselected from R⁹; each R⁹ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl, C₂-C₇alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂, —COOH, —CN or—NO₂; each Q¹ is independently a phenyl ring or a 5- or 6-memberedsaturated or unsaturated heterocyclic ring, each ring optionallysubstituted with one or more substituents independently selected fromhalogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆dialkylamino, —CN, —NO₂, —C(W)N(R¹⁰)R¹¹, —C(O)OR¹¹ and R¹²; each R¹⁰ isindependently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl,C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl; each R¹¹ is independentlyH; or C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl or R¹²; eachR¹² is independently a phenyl ring or a pyridinyl ring, each ringoptionally substituted with one or more substituents independentlyselected from R¹³; each R¹³ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl, C₂-C₇alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂, —COOH, —CN or—NO₂; R²¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl,C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl; R²² is H; or C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl orC₄-C₇ cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²³; each R²³ is independentlyhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN or —NO₂; or a phenyl ring or apyridinyl ring, each ring optionally substituted with one or moresubstituents independently selected from R²⁴; each R²⁴ is independentlyhalogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄alkoxycarbonyl, C₂-C₇ alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl,—OH, —NH₂, —COOH, —CN or —NO₂; R²⁵ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²⁶; each R²⁶ is independentlyhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₂-C₇ alkylcarbonyl, C₂-C₇alkoxycarbonyl, —CN or —NO₂; or a phenyl ring or a pyridinyl ring, eachring optionally substituted with one or more substituents independentlyselected from R²⁷; each R²⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆dialkylamino, C₂-C₄ alkylcarbonyl, C₂-C₄ alkoxycarbonyl, C₂-C₇alkylaminocarbonyl, C₃-C₇ dialkylaminocarbonyl, —OH, —NH₂, —COOH, —CN or—NO₂; R²⁸ is H, halogen, —CN, —NO₂, C₂-C₇ alkylcarbonyl, C₂-C₇haloalkylcarbonyl, C₂-C₇ alkoxycarbonyl, C₂-C₇ alkylaminocarbonyl, C₃-C₇dialkylaminocarbonyl, C₁-C₆ alkylsulfonyl or C₁-C₆ haloalkylsulfonyl; orR²⁸ is C₁-C₆ alkyl, C₃-C₆ cycloalkyl, (C₁-C₆ alkoxy)-(C₁-C₆ alkyl) orC₁-C₆ alkylthio, each optionally substituted with halogen, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₁-C₆ cycloalkyl, C₁-C₆ halocycloalkyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, —CN or —NO₂; R²⁹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R²⁶; each W is independently Oor S; p is 0, 1 or 2; and n is 1 or
 2. 2. A compound of claim 1 whereinA¹ and A² are CR³; A³ is CR³ or N; B¹, B² and B³ are CR²; R¹ is C₁-C₃alkyl optionally substituted with one or more substituents independentlyselected from R⁶; each R² is independently H, halogen, C₁-C₆ haloalkyl,C₁-C₆ haloalkoxy or —CN; each R³ is independently H, halogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ haloalkenyl, C₂-C₆ alkynyl,C₃-C₆ haloalkynyl, C₃-C₆ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,—N(R⁴)R⁵, —C(W)N(R⁴)R⁵, —CN or —NO₂; each R⁴ is independently H, C₁-C₄alkyl, C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl; each R⁵ isindependently H; or C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R⁷; each R⁷ is independently halogen, C₁-C₄ alkyl, C₁-C₄alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CN,—NO₂ or Q¹; Q¹ is a phenyl ring, a pyridinyl ring, a thiazolyl ring, apyrazolyl ring, a triazolyl ring or an imidazolyl ring, each ringoptionally substituted with one or more substituents independentlyselected from halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, —CN,—C(W)N(R¹⁰)R¹¹, C(O)OR¹¹ and R¹²; each R¹⁰ is independently H, C₁-C₄alkyl, C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl; and each R¹¹ isindependently H; or C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl or R¹².
 3. Acompound of claim 2 wherein Q is a phenyl ring, a pyridinyl ring, apyrimidinyl ring, a triazinyl ring, a pyrazolyl ring, a triazolyl ring,a tetrazolyl ring, an imidazolyl ring, an oxazolyl ring, an isoxazolylring, a thiazolyl ring or an isothiazolyl ring, each ring optionallysubstituted with one or more substituents independently selected fromhalogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, —CN, —N(R⁴)R⁵; —C(W)N(R⁴)R⁵,—C(O)OR⁵ and R⁸.
 4. A compound of claim 3 wherein R¹ is C₁-C₃ alkyloptionally substituted with halogen; each R² is independently H, CF₃,OCF₃, halogen or —CN; each R³ is independently H, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl, C₃-C₄haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN or —NO₂; eachR⁴ is H; Q is a pyrazolyl ring, a triazolyl ring, a tetrazolyl ring oran imidazolyl ring, each ring attached through nitrogen and optionallysubstituted with one or more substituents independently selected fromhalogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, —CN, —NO₂, —N(R⁴)R⁵,—C(W)N(R⁴)R⁵, —C(O)OR⁵ and R⁸; and W is O.
 5. A compound of claim 4wherein A³ is CR³; B² is CH; R¹ is CF₃; each R² is independently H orhalogen; each R³ is independently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or—NO₂; and Q is a pyrazolyl ring, a triazolyl ring, a tetrazolyl ring oran imidazolyl ring, each ring attached through nitrogen and optionallysubstituted with one or more substituents independently selected fromhalogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, —CN and —NH₂.
 6. A compound ofclaim 2 wherein Q is —S(O)₂N(R²¹)R²², —S(O)_(p)R²⁵ or —S(O)(═NR²⁸)R²⁹;R²¹ is H or C₁-C₆ alkyl; R²² is C₁-C₄ alkyl optionally substituted withone or more substituents independently selected from R²³; each R²³ isindependently halogen, C₁-C₄ alkylthio, —CN, a phenyl ring or apyridinyl ring; R²⁵ is C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R²⁶; and each R²⁶ is independently halogen, C₁-C₄ alkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —CN or —NO₂;R²⁸ is H, halogen, C₁-C₄ alkyl, —CN, —NO₂, haloalkylcarbonyl or C₂-C₇alkoxycarbonyl; and R²⁹ is C₁-C₄ alkyl; C₃-C₄ alkenyl, C₃-C₄ alkynyl,C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R²⁶.
 7. A compound of claim 6 wherein R¹ is C₁-C₃ alkyloptionally substituted with halogen; each R² is independently H, CF₃,OCF₃, halogen or —CN; each R³ is independently H, halogen, C₁-C₄ alkyl,haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl, C₃-C₄haloalkynyl, cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN or —NO₂; eachR⁴ is H; Q is —S(O)₂N(R²¹)R²²; R²¹ is H or methyl; and W is O.
 8. Acompound of claim 7 wherein A³ is CR³; B² is CH; R¹ is CF₃; each R² isindependently H or halogen; and each R³ is independently H, halogen,C₁-C₂ alkyl, —C≡CH, —CN or —NO₂.
 9. A compound of claim 6 wherein R¹ isC₁-C₃ alkyl optionally substituted with halogen; each R² isindependently H, CF₃, OCF₃, halogen or —CN; each R³ is independently H,halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₃-C₄ haloalkenyl,C₂-C₄ alkynyl, C₃-C₄ haloalkynyl, cyclopropyl, C₁-C₄ alkoxy,—C(W)N(R⁴)R⁵, —CN or —NO₂; each R⁴ is H; Q is —S(O)_(p)R²⁵; R²⁵ is C₁-C₄alkyl optionally substituted with one or more substituents independentlyselected from R²⁶; each R²⁶ is independently halogen or —CN; W is O; andp is 1 or
 2. 10. A compound of claim 9 wherein A³ is CR³; B² is CH; R¹is CF₃; each R² is independently H or halogen; and each R³ isindependently H, halogen, C₁-C₂ alkyl, —C≡CH, —CN or —NO₂.
 11. Acompound of claim 6 wherein R¹ is C₁-C₃ alkyl optionally substitutedwith halogen; each R² is independently H, CF₃, OCF₃, halogen or —CN;each R³ is independently H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkenyl, C₃-C₄ haloalkenyl, C₂-C₄ alkynyl, C₃-C₄ haloalkynyl,cyclopropyl, C₁-C₄ alkoxy, —C(W)N(R⁴)R⁵, —CN or —NO₂; each R⁴ is H; Q is—S(O)(═NR²⁸)R²⁹; R²⁸ is H, C₁-C₄ alkyl, —CN or —NO₂; R²⁹ is C₁-C₄ alkyloptionally substituted with one or more substituents independentlyselected from R²⁶; each R²⁶ is independently halogen or —CN; and W is O.12. A compound of claim 11 wherein A³ is CR³; B² is CH; R¹ is CF₃; eachR² is independently H or halogen; and each R³ is independently H,halogen, C₁-C₂ alkyl, —C≡CH, —CN or —NO₂.
 13. A compound of claim 1 thatis selected from the group consisting of:5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-(1H-pyrazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;2-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]pyridine;5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)isoxazole;1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]-1H-1,2,4-triazole;1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylphenyl]-1H-1,2,4-triazole;1-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylphenyl]-1H-1,2,3-triazole;5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile;5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,3-triazol-1-yl)benzenecarbothioamide;2-(3-amino-1H-1,2,4-triazol-1-yl)-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]benzonitrile;5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-tetrazol-1-yl)benzonitrile;N-(cyclopropylmethyl)-4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzenesulfonamide;4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(2-pyridinylmethyl)benzenesulfonamide;5-[5-(3,5-dibromophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile;5-[5-(3,5-dichlorophenyl)-4,5-dihydro-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)isoxazole;5-[(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylsulfonyl)benzonitrile;and3-[3-bromo-4-(methylthio)phenyl]-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole.14. A composition comprising a compound of claim 1 and at least oneadditional component selected from the group consisting of a surfactant,a solid diluent and a liquid diluent, said composition optionallyfurther comprising at least one additional biologically active compoundor agent.
 15. A composition for controlling an invertebrate pestcomprising a biologically effective amount of a compound of claim 1 andat least one additional component selected from the group consisting ofa surfactant, a solid diluent and a liquid diluent, said compositionoptionally further comprising a biologically effective amount of atleast one additional biologically active compound or agent.
 16. Thecomposition of claim 15 wherein at least one additional biologicallyactive compound or agent is selected from insecticides of the groupconsisting of macrocyclic lactones, neonicotinoids, octopamine receptorligands, ryanodine receptor ligands, ecdysone agonists, sodium channelmodulators, chitin synthesis inhibitors, nereisotoxin analogs,mitochondrial electron transport inhibitors, cholinesterase inhibitors,cyclodiene insecticides, molting inhibitors, GABA-regulated chloridechannel blockers, juvenile hormone mimics, lipid biosynthesis inhibitorsand biological agents including nucleopolyhedrovirus, a member ofBacillus thuringiensis, an encapsulated delta-endotoxin of Bacillusthuringiensis; and a naturally occurring or a genetically modified viralinsecticide.
 17. The composition of claim 15 wherein at least oneadditional biologically active compound or agent is selected from thegroup consisting of abamectin, acephate, acetamiprid, acetoprole,aldicarb, amidoflumet, amitraz, avermectin, azadirachtin,azinphos-methyl, bifenthrin, bifenazate, bistrifluoron, buprofezin,carbofuran, cartap, chinomethionat, chlorfenapyr, chlorfluazuron,chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, chlorobenzilate,chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin,cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyhexatin,cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon-dicofol,dieldrin, dienochlor, diflubenzuron, dimefluthrin, dimethoate,dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate,ethiprole, etoxazole, fenamiphos, fenazaquin, fenbutatin oxide,fenothiocarb, fenoxycarb; fenpropathrin, fenpyroximate, fenvalerate,fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate,flufenerim, flufenoxuron, fonophos, halofenozide, hexaflumuron,hexythiazox, hydramethylnon, imicyafos, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine,novaluron, noviflumuron, oxamyl, parathion, parathion-methyl,permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,profenofos, profluthrin, propargite, protrifenbute, pymetrozine,pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon,pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad,spiridiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide,tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad,tralomethrin, triazamate, trichlorfon, triflumuron, Bacillusthuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki,nucleopolyhedrovirus, an encapsulated delta-endotoxin of Bacillusthuringiensis, baculovirus, entomopathogenic bacteria, entomopathogenicvirus and entomopathogenic fungi.
 18. The composition of claim 17wherein at least one additional biologically active compound or agent isselected from the group consisting of abamectin, acetamiprid, amitraz,avermectin, azadirachtin, bifenthrin, buprofezin, cartap,chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin,cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin,cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran,diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole,fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid,flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, imidacloprid,indoxacarb, lufenuron, metaflumizone, methomyl, methoprene,methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine,pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram,spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus and an encapsulateddelta-endotoxin of Bacillus thuringiensis.
 19. The composition of claim15 in the form of a soil drench liquid formulation.
 20. A spraycomposition for controlling an invertebrate pest, comprising: (a) abiologically effective amount of the compound of claim 1 or thecomposition of claim 15; and (b) a propellant.
 21. A bait compositionfor controlling an invertebrate pest, comprising: (b) biologicallyeffective amount of the compound of claim 1 or the composition of claim15; (b) one or more food materials; (c) optionally an attractant; and(d) optionally a humectant.
 22. A trap device for controlling aninvertebrate pest, comprising: (a) the bait composition of claim 21; and(b) a housing adapted to receive the bait composition, wherein thehousing has at least one opening sized to permit the invertebrate pestto pass through the opening so the invertebrate pest can gain access tothe bait composition from a location outside the housing, and whereinthe housing is further adapted to be placed in or near a locus ofpotential or known activity for the invertebrate pest.
 23. A method forcontrolling an invertebrate pest comprising contacting the invertebratepest or its environment with a biologically effective amount of acompound of claim
 1. 24. A method for controlling an invertebrate pestcomprising contacting the invertebrate pest or its environment with acomposition of claim
 15. 25. The method of claim 24 wherein theenvironment is soil and the composition is applied to the soil as a soildrench formulation.
 26. A method for controlling a cockroach, an ant ora termite, comprising contacting a cockroach, an ant, or a termite withthe bait composition in the trap device of claim
 22. 27. A method forcontrolling a mosquito, a black fly, a stable, fly, a deer fly, a horsefly, a wasp, a yellow jacket, a hornet, a tick, a spider, an ant, or agnat, comprising contacting a mosquito, a black fly, a stable, fly, adeer fly, a horse fly, a wasp, a yellow jacket, a hornet, a tick, aspider, an ant, or a gnat with the spray composition of claim 20dispensed from a spray container.
 28. A method for protecting a seedfrom an invertebrate pest comprising contacting the seed with abiologically effective amount of a compound of claim
 1. 29. The methodof claim 28 wherein the seed is coated with the compound of claim 1formulated as a composition comprising a film former or adhesive agent.30. A treated seed comprising a compound of claim 1 in an amount of fromabout 0.0001 to 1% by weight of the seed before treatment.
 31. Acomposition for protecting an animal from an invertebrate parasitic pestcomprising a parasiticidally effective amount of a compound of claim 1and at least one carrier.
 32. The composition of claim 31 in a form fororal administration.
 33. A method for protecting an animal from aninvertebrate parasitic pest comprising administering to the animal aparasiticidally effective amount of a compound of claim 1.